SK852001A3 - Method for producing ortho-alkylated benzoic acid derivatives - Google Patents

Method for producing ortho-alkylated benzoic acid derivatives Download PDF

Info

Publication number: SK852001A3
Authority: SK; Slovakia
Prior art keywords: methyl; acid; chloro; methylsulfonyl; give
Prior art date: 1998-07-23

Application number

SK85-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Ekkehard Bartmann

Ingeborg Stein

Original Assignee

Merck Patent Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-07-23

Filing date

1999-07-06

Publication date

2001-08-06

1999-07-06 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2001-08-06 Publication of SK852001A3 publication Critical patent/SK852001A3/sk

Links

150000001558 benzoic acid derivatives Chemical class 0.000 title claims abstract description 16
238000004519 manufacturing process Methods 0.000 title abstract description 6
150000001499 aryl bromides Chemical class 0.000 claims abstract description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 47
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 46
XXFKOBGFMUIWDH-UHFFFAOYSA-N 4-chloro-2-methylbenzoic acid Chemical compound CC1=CC(Cl)=CC=C1C(O)=O XXFKOBGFMUIWDH-UHFFFAOYSA-N 0.000 claims description 35
238000000034 method Methods 0.000 claims description 33
238000002360 preparation method Methods 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 24
239000001569 carbon dioxide Substances 0.000 claims description 23
229910002092 carbon dioxide Inorganic materials 0.000 claims description 23
229910052744 lithium Inorganic materials 0.000 claims description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
YGYZEHXIHONBML-UHFFFAOYSA-N 4-chloro-2-methyl-5-methylsulfonylbenzoic acid Chemical compound CC1=CC(Cl)=C(S(C)(=O)=O)C=C1C(O)=O YGYZEHXIHONBML-UHFFFAOYSA-N 0.000 claims description 17
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 17
RTIPTGMVQIIMKL-UHFFFAOYSA-N 1-bromo-4-chloro-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1Br RTIPTGMVQIIMKL-UHFFFAOYSA-N 0.000 claims description 16
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 16
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 16
-1 4-benzylamino-5-methylsulfonyl-2-methylbenzoic acid ester Chemical class 0.000 claims description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 13
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 13
229920006395 saturated elastomer Polymers 0.000 claims description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
239000011541 reaction mixture Substances 0.000 claims description 12
GROMEQPXDKRRIE-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4,5-bis(methylsulfonyl)benzamide Chemical compound CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N GROMEQPXDKRRIE-UHFFFAOYSA-N 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
OBYSQDHKQUWQEW-UHFFFAOYSA-N 2-methyl-4,5-bis(methylsulfonyl)benzoic acid Chemical compound CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(O)=O OBYSQDHKQUWQEW-UHFFFAOYSA-N 0.000 claims description 10
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
239000012442 inert solvent Substances 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
UADMBZFZZOBWBB-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-pyrrol-1-ylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(N2C=CC=C2)=C1S(C)(=O)=O UADMBZFZZOBWBB-UHFFFAOYSA-N 0.000 claims description 9
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 8
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 8
235000010265 sodium sulphite Nutrition 0.000 claims description 8
WCBNPNGDKPWXSF-UHFFFAOYSA-N 4-(benzylamino)-2-methyl-5-methylsulfonylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(NCC=2C=CC=CC=2)=C1S(C)(=O)=O WCBNPNGDKPWXSF-UHFFFAOYSA-N 0.000 claims description 7
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 5
239000003208 petroleum Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims description 4
KBPZKRMZEPBEBY-UHFFFAOYSA-N 2-methyl-4,5-bis(methylsulfonyl)benzoyl chloride Chemical compound CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(Cl)=O KBPZKRMZEPBEBY-UHFFFAOYSA-N 0.000 claims description 4
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 claims description 4
YSQFBLFEYNOIBW-UHFFFAOYSA-N lithium;cyclopropane Chemical compound [Li+].C1C[CH-]1 YSQFBLFEYNOIBW-UHFFFAOYSA-N 0.000 claims description 4
SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 claims description 4
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 3
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
CJKJNTJPOYSDQL-UHFFFAOYSA-N 2-methylsulfonylbenzamide Chemical compound CS(=O)(=O)C1=CC=CC=C1C(N)=O CJKJNTJPOYSDQL-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
239000000543 intermediate Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000002244 precipitate Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
239000012452 mother liquor Substances 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
239000005457 ice water Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
229960001922 sodium perborate Drugs 0.000 description 3
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
ORKKSDGNUXWYKI-UHFFFAOYSA-N 2-methyl-5-methylsulfonyl-4-pyrrol-1-ylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(N2C=CC=C2)=C1S(C)(=O)=O ORKKSDGNUXWYKI-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001503 aryl iodides Chemical class 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000021523 carboxylation Effects 0.000 description 2
238000006473 carboxylation reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012467 final product Substances 0.000 description 2
239000012847 fine chemical Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
KLPYAEJECLFJHX-UHFFFAOYSA-N methyl 2-methyl-5-methylsulfonyl-4-pyrrol-1-ylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(S(C)(=O)=O)=C1N1C=CC=C1 KLPYAEJECLFJHX-UHFFFAOYSA-N 0.000 description 2
CENDNMZQRHKPMC-UHFFFAOYSA-N methyl 4-(benzylamino)-2-methyl-5-methylsulfonylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(S(C)(=O)=O)=C1NCC1=CC=CC=C1 CENDNMZQRHKPMC-UHFFFAOYSA-N 0.000 description 2
QBVGRWIWDJZYAP-UHFFFAOYSA-N methyl 4-amino-2-methyl-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(N)C=C1C QBVGRWIWDJZYAP-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
XGYLSRFSXKAYCR-UHFFFAOYSA-N 2-chloro-4-methylaniline Chemical compound CC1=CC=C(N)C(Cl)=C1 XGYLSRFSXKAYCR-UHFFFAOYSA-N 0.000 description 1
MYJUBDJLKREUGU-UHFFFAOYSA-N 2-chloro-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(Cl)=C1 MYJUBDJLKREUGU-UHFFFAOYSA-N 0.000 description 1
MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
YYFHHBYKGNGHHU-UHFFFAOYSA-N 4-chloro-2,5-dimethylbenzoic acid Chemical compound CC1=CC(C(O)=O)=C(C)C=C1Cl YYFHHBYKGNGHHU-UHFFFAOYSA-N 0.000 description 1
ZIOGCIPQDRCAKY-UHFFFAOYSA-N 4-chloro-2-iodo-1-methylbenzene Chemical compound CC1=CC=C(Cl)C=C1I ZIOGCIPQDRCAKY-UHFFFAOYSA-N 0.000 description 1
XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
XGAFCCUNHIMIRV-UHFFFAOYSA-N 4-chloropyridine;hydron;chloride Chemical compound Cl.ClC1=CC=NC=C1 XGAFCCUNHIMIRV-UHFFFAOYSA-N 0.000 description 1
PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
241000349731 Afzelia bipindensis Species 0.000 description 1
102000003669 Antiporters Human genes 0.000 description 1
108090000084 Antiporters Proteins 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
238000000297 Sandmeyer reaction Methods 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
238000006138 lithiation reaction Methods 0.000 description 1
CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
238000001465 metallisation Methods 0.000 description 1
INGSNHMAAYVQPH-UHFFFAOYSA-N methyl 4-chloro-2-methyl-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(Cl)C=C1C INGSNHMAAYVQPH-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000004476 plant protection product Substances 0.000 description 1
238000007747 plating Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
WBGSMIRITKHZNA-UHFFFAOYSA-M trisodium;dioxido(oxidooxy)borane Chemical compound [Na+].[Na+].[Na+].[O-]OB([O-])[O-] WBGSMIRITKHZNA-UHFFFAOYSA-M 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B18/00—Use of agglomerated or waste materials or refuse as fillers for mortars, concrete or artificial stone; Treatment of agglomerated or waste materials or refuse, specially adapted to enhance their filling properties in mortars, concrete or artificial stone
- C04B18/02—Agglomerated materials, e.g. artificial aggregates
- C04B18/021—Agglomerated materials, e.g. artificial aggregates agglomerated by a mineral binder, e.g. cement
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
- C04B2111/00474—Uses not provided for elsewhere in C04B2111/00
- C04B2111/00767—Uses not provided for elsewhere in C04B2111/00 for waste stabilisation purposes
- C04B2111/00775—Uses not provided for elsewhere in C04B2111/00 for waste stabilisation purposes the composition being used as waste barriers or the like, e.g. compositions used for waste disposal purposes only, but not containing the waste itself
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/91—Use of waste materials as fillers for mortars or concrete

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Civil Engineering (AREA)
Ceramic Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Materials Engineering (AREA)
Structural Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK85-2001A 1998-07-23 1999-07-06 Method for producing ortho-alkylated benzoic acid derivatives SK852001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE1998133118 DE19833118C2 (de)	1998-07-23	1998-07-23	Verfahren zur Herstellung von orthoalkylierten Benzoesäurederivaten
PCT/EP1999/004674 WO2000005187A1 (de)	1998-07-23	1999-07-06	Verfahren zur herstellung von ortho-alkylierten benzoesäurederivaten

Publications (1)

Publication Number	Publication Date
SK852001A3 true SK852001A3 (en)	2001-08-06

Family

ID=7875019

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK85-2001A SK852001A3 (en)	1998-07-23	1999-07-06	Method for producing ortho-alkylated benzoic acid derivatives

Country Status (23)

Country	Link
US (3)	US6350904B1 (id)
EP (1)	EP1098866B1 (id)
JP (1)	JP2002521352A (id)
KR (1)	KR20010053294A (id)
CN (1)	CN1190406C (id)
AR (1)	AR020620A1 (id)
AT (1)	ATE259343T1 (id)
AU (1)	AU756673B2 (id)
BR (1)	BR9912319A (id)
CA (1)	CA2338300A1 (id)
DE (2)	DE19833118C2 (id)
DK (1)	DK1098866T3 (id)
ES (1)	ES2216540T3 (id)
HK (1)	HK1039478A1 (id)
HU (1)	HUP0102657A3 (id)
ID (1)	ID27856A (id)
NO (1)	NO20010365L (id)
PL (1)	PL345284A1 (id)
PT (1)	PT1098866E (id)
SK (1)	SK852001A3 (id)
TW (1)	TW546285B (id)
WO (1)	WO2000005187A1 (id)
ZA (1)	ZA200101507B (id)

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JP2005505045A (ja)	2001-09-28	2005-02-17	コムヴォールト・システムズ・インコーポレーテッド	クイックリカバリボリュームを作成及び管理する方法及び装置
CA2508089A1 (en)	2002-10-07	2004-04-22	Commvault Systems, Inc.	System and method for managing stored data
US7734578B2 (en)	2003-11-13	2010-06-08	Comm Vault Systems, Inc.	System and method for performing integrated storage operations
US8959299B2 (en) *	2004-11-15	2015-02-17	Commvault Systems, Inc.	Using a snapshot as a data source
DE102005005946A1 (de) *	2005-02-10	2006-08-17	Basf Ag	Verfahren zur Herstellung tertiärer Phosphine
US7928591B2 (en) *	2005-02-11	2011-04-19	Wintec Industries, Inc.	Apparatus and method for predetermined component placement to a target platform
JP4641839B2 (ja) *	2005-03-23	2011-03-02	セントラル硝子株式会社	４−メチル−３−トリフルオロメチル安息香酸の製造方法
US20100312013A1 (en) *	2009-06-03	2010-12-09	Boehringer Ingelheim International Gmbh	Steroselective synthesis of certain trifluoromethyl-substituted alcohols
US8719767B2 (en)	2011-03-31	2014-05-06	Commvault Systems, Inc.	Utilizing snapshots to provide builds to developer computing devices
US9092500B2 (en)	2009-09-03	2015-07-28	Commvault Systems, Inc.	Utilizing snapshots for access to databases and other applications
US8433682B2 (en) *	2009-12-31	2013-04-30	Commvault Systems, Inc.	Systems and methods for analyzing snapshots
WO2011082138A1 (en)	2009-12-31	2011-07-07	Commvault Systems, Inc.	Systems and methods for performing data management operations using snapshots
KR20140048891A (ko) *	2011-05-27	2014-04-24	템플 유니버시티-오브 더 커먼웰쓰 시스템 오브 하이어 에듀케이션	치환된 2-벤질리덴-2H-벤조[b][1,4]티아진-3(4H)-온, 이의 유도체, 및 이의 치료적 용도
CN106365978B (zh) *	2016-08-31	2019-01-11	绍兴上虞华伦化工有限公司	一种2,3-二氟-6-甲氧基苯甲酸的制备方法
CN115448831B (zh) *	2022-11-10	2023-02-03	北京元延医药科技股份有限公司	制备4-乙酰基-1-萘甲酸的方法
CN116425623B (zh) *	2023-04-10	2024-02-13	大连凯飞化学股份有限公司	一锅法合成3,5-二氯-4-甲基苯甲酸的方法

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GB8613207D0 (en) *	1986-05-30	1986-07-02	Yarsley Technical Centre Ltd	Trifluoromethyl aromatic compounds
EP0589336B1 (de) *	1992-09-22	1997-01-08	Hoechst Aktiengesellschaft	Benzoylguanidine, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Antiarrhythmika
DE4430213A1 (de) *	1994-08-28	1996-02-29	Merck Patent Gmbh	Arylbenzoylguanidine
DE4430861A1 (de) *	1994-08-31	1996-03-07	Merck Patent Gmbh	Heterocyclyl-benzoylguanidine
DE19529612A1 (de) *	1995-08-11	1997-02-13	Merck Patent Gmbh	Sulfonyl- oder Sulfinyl-benzoylguanidin-Derivate

1998
- 1998-07-23 DE DE1998133118 patent/DE19833118C2/de not_active Expired - Fee Related
1999
- 1999-07-06 PT PT99934577T patent/PT1098866E/pt unknown
- 1999-07-06 DK DK99934577T patent/DK1098866T3/da active
- 1999-07-06 AT AT99934577T patent/ATE259343T1/de not_active IP Right Cessation
- 1999-07-06 ID ID20010281A patent/ID27856A/id unknown
- 1999-07-06 WO PCT/EP1999/004674 patent/WO2000005187A1/de not_active Ceased
- 1999-07-06 CN CNB998090085A patent/CN1190406C/zh not_active Expired - Fee Related
- 1999-07-06 HK HK02101006.8A patent/HK1039478A1/zh unknown
- 1999-07-06 ES ES99934577T patent/ES2216540T3/es not_active Expired - Lifetime
- 1999-07-06 EP EP19990934577 patent/EP1098866B1/de not_active Expired - Lifetime
- 1999-07-06 PL PL34528499A patent/PL345284A1/xx unknown
- 1999-07-06 SK SK85-2001A patent/SK852001A3/sk unknown
- 1999-07-06 HU HU0102657A patent/HUP0102657A3/hu unknown
- 1999-07-06 AU AU50314/99A patent/AU756673B2/en not_active Ceased
- 1999-07-06 DE DE59908523T patent/DE59908523D1/de not_active Expired - Fee Related
- 1999-07-06 JP JP2000561144A patent/JP2002521352A/ja active Pending
- 1999-07-06 KR KR1020007015017A patent/KR20010053294A/ko not_active Withdrawn
- 1999-07-06 US US09/744,302 patent/US6350904B1/en not_active Expired - Fee Related
- 1999-07-06 BR BR9912319A patent/BR9912319A/pt not_active IP Right Cessation
- 1999-07-06 CA CA 2338300 patent/CA2338300A1/en not_active Abandoned
- 1999-07-21 TW TW88112363A patent/TW546285B/zh active
- 1999-07-23 AR ARP990103626 patent/AR020620A1/es not_active Application Discontinuation
2001
- 2001-01-22 NO NO20010365A patent/NO20010365L/no unknown
- 2001-02-22 ZA ZA200101507A patent/ZA200101507B/en unknown
2002
- 2002-01-08 US US10/038,602 patent/US6515143B2/en not_active Expired - Fee Related
- 2002-10-08 US US10/265,607 patent/US6573404B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
BR9912319A (pt)	2001-05-08
EP1098866A1 (de)	2001-05-16
US20030069444A1 (en)	2003-04-10
HK1039478A1 (zh)	2002-04-26
US6573404B2 (en)	2003-06-03
CA2338300A1 (en)	2000-02-03
CN1190406C (zh)	2005-02-23
US6350904B1 (en)	2002-02-26
KR20010053294A (ko)	2001-06-25
AR020620A1 (es)	2002-05-22
PL345284A1 (en)	2001-12-03
EP1098866B1 (de)	2004-02-11
NO20010365D0 (no)	2001-01-22
JP2002521352A (ja)	2002-07-16
DK1098866T3 (da)	2004-06-01
NO20010365L (no)	2001-01-22
HUP0102657A2 (hu)	2001-11-28
AU756673B2 (en)	2003-01-23
AU5031499A (en)	2000-02-14
DE19833118C2 (de)	2000-07-27
TW546285B (en)	2003-08-11
DE59908523D1 (de)	2004-03-18
CN1310700A (zh)	2001-08-29
US6515143B2 (en)	2003-02-04
HUP0102657A3 (en)	2002-03-28
WO2000005187A1 (de)	2000-02-03
ZA200101507B (en)	2002-05-22
PT1098866E (pt)	2004-06-30
ES2216540T3 (es)	2004-10-16
ID27856A (id)	2001-04-26
DE19833118A1 (de)	2000-02-03
US20020091286A1 (en)	2002-07-11
ATE259343T1 (de)	2004-02-15

Publication	Publication Date	Title
SK852001A3 (en)	2001-08-06	Method for producing ortho-alkylated benzoic acid derivatives
US2937204A (en)	1960-05-17	Nu-alkanoyl dinitrobenzamides
JPH0625205B2 (ja)	1994-04-06	置換サツカリン化合物及びそれを含有する硬化性組成物
US4661636A (en)	1987-04-28	6-sulfoxyphenol derivatives, their preparation and their use as cytoprotective agents
JPH03135983A (ja)	1991-06-10	１，１―ジオキソ―７―置換セフェムの製造方法
JPH04502150A (ja)	1992-04-16	２―（クロロ，ブロモ，またはニトロ）―４―（アルキルスルフォニル）安息香酸の調製および中間体
CZ2001176A3 (cs)	2001-05-16	Způsob přípravy derivátu benzoové kyseliny alkylovaného v poloze orto
JPH0623168B2 (ja)	1994-03-30	ベンゼンスルホニルクロリド誘導体の製造方法
GB2159156A (en)	1985-11-27	Process for the preparation of alkyl 3-chlorosulfonylthiophene-2-carboxylate
JPH06247918A (ja)	1994-09-06	フェニルベンズアミド誘導体の製造方法
MXPA01000764A (en)	2001-12-04	Method for producing ortho-alkylated benzoic acid derivatives
JPS61100570A (ja)	1986-05-19	ピラゾ−ル誘導体の製法
CN1136195C (zh)	2004-01-28	3-烃基-5-吡唑羧酸酯的合成方法
JP2648346B2 (ja)	1997-08-27	ハロゲノイサト酸無水物の製法
USH504H (en)	1988-08-02	Process for the preparation of alkyl 3-chlorosulfonylthiophene-2-carboxylate
CN121895184A (zh)	2026-04-21	一种含硫烷基基团取代的联芳烃类化合物的制备方法
KR100322237B1 (ko)	2002-03-29	α-케토카르복시산 유도체의 제조방법
JP2500316B2 (ja)	1996-05-29	１，４，５，８―テトラキス（ハロゲノメチル）ナフタレン誘導体、およびその製造方法
JPS61109771A (ja)	1986-05-28	ピラゾ−ル誘導体およびその製法
JPS61165353A (ja)	1986-07-26	オルソニトロアニリンとその製造法
JPS6256467A (ja)	1987-03-12	フエニルチオグリコ−ル酸誘導体の製造法
JP2001081068A (ja)	2001-03-27	シクロヘキセン誘導体
JPH02255653A (ja)	1990-10-16	１，４，５，８―テトラキス（メルカプトメチル）ナフタレン、その誘導体及びこれらの製造方法
EP1411048A1 (en)	2004-04-21	Preparation of 2-bromo-pyrimidines and 2-iodo-pyrimidines
JPH0832679B2 (ja)	1996-03-29	Ｎ―フタルイシド誘導体及びその製造法