CA1048509A - Composes de type 4-(0-halophenyl)-1,2,4-triazole-3-thiol - Google Patents

Composes de type 4-(0-halophenyl)-1,2,4-triazole-3-thiol

Info

Publication number: CA1048509A
Authority: CA; Canada
Prior art keywords: triazole; thiol; chloro; methyl; hydrogen
Prior art date: 1974-03-07
Legal status (The legal status 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 status listed.): Expired

Application number

CA78301999A

Other languages

English (en)

Inventor

Charles J. Paget (Jr.)

James H. Wikel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

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.)

1974-03-07

Filing date

1978-04-26

Publication date

1979-02-13

1974-03-07 Priority claimed from US05/449,141 external-priority patent/US3937713A/en

1978-04-26 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1979-02-13 Application granted granted Critical

1979-02-13 Publication of CA1048509A publication Critical patent/CA1048509A/fr

Status Expired legal-status Critical Current

Links

-1 C1-C11 alkyl Chemical group 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
125000001246 bromo group Chemical group Br* 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002431 hydrogen Chemical group 0.000 claims description 9
238000006210 cyclodehydration reaction Methods 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
UZUGWJJKPMBHMF-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1C1=CC=C(Cl)C=C1Cl UZUGWJJKPMBHMF-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
KCBMFIARZKLAAZ-UHFFFAOYSA-N 4-(2,6-dichlorophenyl)-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NN=C(S)N1C1=C(Cl)C=CC=C1Cl KCBMFIARZKLAAZ-UHFFFAOYSA-N 0.000 claims description 2
OQWDXYHETGASHD-UHFFFAOYSA-N 4-(2-chloro-5-methylphenyl)-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NN=C(S)N1C1=CC(C)=CC=C1Cl OQWDXYHETGASHD-UHFFFAOYSA-N 0.000 claims description 2
ZQGROUIPNHTYAV-UHFFFAOYSA-N 4-(2-chlorophenyl)-1h-1,2,4-triazole-5-thione Chemical compound SC1=NN=CN1C1=CC=CC=C1Cl ZQGROUIPNHTYAV-UHFFFAOYSA-N 0.000 claims description 2
LUQHKHZFLFXGMZ-UHFFFAOYSA-N 4-(2-chlorophenyl)-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1C1=CC=CC=C1Cl LUQHKHZFLFXGMZ-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
RQFBFIINZDCVKJ-UHFFFAOYSA-N 4-[2-chloro-5-(trifluoromethyl)phenyl]-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NN=C(S)N1C1=CC(C(F)(F)F)=CC=C1Cl RQFBFIINZDCVKJ-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 6
BGFURDBGMRKOTL-UHFFFAOYSA-N [1,2,4]triazolo[3,4-b][1,3]benzothiazole Chemical class C1=CC=C2N3C=NN=C3SC2=C1 BGFURDBGMRKOTL-UHFFFAOYSA-N 0.000 abstract description 3
244000000003 plant pathogen Species 0.000 abstract 1
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 17
238000000034 method Methods 0.000 description 16
238000004458 analytical method Methods 0.000 description 10
239000002585 base Substances 0.000 description 10
238000006073 displacement reaction Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
238000002844 melting Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
125000000217 alkyl group Chemical group 0.000 description 7
150000002367 halogens Chemical class 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
150000003583 thiosemicarbazides Chemical class 0.000 description 4
UHYISDCXHNDRHZ-UHFFFAOYSA-N 7h-[1,3]thiazolo[5,4-e]benzotriazole Chemical class C1=CC2=NCSC2=C2N=NN=C21 UHYISDCXHNDRHZ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
PAPCIKSAPRAMIS-UHFFFAOYSA-N 5-fluoro-7h-[1,3]thiazolo[5,4-e]benzotriazole Chemical compound FC1=CC2=NN=NC2=C2SCN=C12 PAPCIKSAPRAMIS-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
241000209094 Oryza Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000002538 fungal effect Effects 0.000 description 2
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
230000006698 induction Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
239000000243 solution Substances 0.000 description 2
150000003511 tertiary amides Chemical class 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
GMZULTAPVYULPI-UHFFFAOYSA-N 1,6-dimethyl-[1,2,4]triazolo[3,4-b][1,3]benzothiazole Chemical compound CC1=CC=C2N3C(C)=NN=C3SC2=C1 GMZULTAPVYULPI-UHFFFAOYSA-N 0.000 description 1
BVMPZALNWNLBMA-UHFFFAOYSA-N 1-(trifluoromethyl)-[1,2,4]triazolo[3,4-b][1,3]benzothiazole Chemical compound C1=CC=C2N3C(C(F)(F)F)=NN=C3SC2=C1 BVMPZALNWNLBMA-UHFFFAOYSA-N 0.000 description 1
ODOTYLQYSDVPMA-UHFFFAOYSA-N 1-iodo-2-isothiocyanatobenzene Chemical compound IC1=CC=CC=C1N=C=S ODOTYLQYSDVPMA-UHFFFAOYSA-N 0.000 description 1
NNUXLZCIOXNCAJ-UHFFFAOYSA-N 1-methyl-7-(trifluoromethyl)-[1,2,4]triazolo[3,4-b][1,3]benzothiazole Chemical compound C1=C(C(F)(F)F)C=C2N3C(C)=NN=C3SC2=C1 NNUXLZCIOXNCAJ-UHFFFAOYSA-N 0.000 description 1
XMEQXRMNVMZFAB-UHFFFAOYSA-N 1-methyl-[1,2,4]triazolo[3,4-b][1,3]benzothiazole Chemical compound C1=CC=C2N3C(C)=NN=C3SC2=C1 XMEQXRMNVMZFAB-UHFFFAOYSA-N 0.000 description 1
LLCOQBODWBFTDD-UHFFFAOYSA-N 1h-triazol-1-ium-4-thiolate Chemical class SC1=CNN=N1 LLCOQBODWBFTDD-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
RYOIZJJJQVKSQQ-UHFFFAOYSA-N 2h-pyrrolo[2,3-g][1,3]benzothiazole Chemical class C1=CC2=NCSC2=C2C=CN=C21 RYOIZJJJQVKSQQ-UHFFFAOYSA-N 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
MLRAJZNPKPVUDQ-UHFFFAOYSA-N 3-sulfanyl-1,2-dihydrotriazole Chemical compound SN1NNC=C1 MLRAJZNPKPVUDQ-UHFFFAOYSA-N 0.000 description 1
ZKCLMUKDVASNII-UHFFFAOYSA-N 4-(2-chloro-6-methylphenyl)-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=CC(Cl)=C1N1C(S)=NN=C1 ZKCLMUKDVASNII-UHFFFAOYSA-N 0.000 description 1
JKTQSJLNEDZVAK-UHFFFAOYSA-N 4-(2-fluorophenyl)-1h-1,2,4-triazole-5-thione Chemical compound FC1=CC=CC=C1N1C(=S)NN=C1 JKTQSJLNEDZVAK-UHFFFAOYSA-N 0.000 description 1
IUUFYANMVJYUEC-UHFFFAOYSA-N 4-(6-bromo-2-fluoro-3-methylphenyl)-3-butyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCC1=NN=C(S)N1C1=C(Br)C=CC(C)=C1F IUUFYANMVJYUEC-UHFFFAOYSA-N 0.000 description 1
CUHCBWKQRDWQMN-UHFFFAOYSA-N 4-ethyl-2,5-dimethylheptane Chemical compound CCC(C)C(CC)CC(C)C CUHCBWKQRDWQMN-UHFFFAOYSA-N 0.000 description 1
OUZCWDMJTKYHCA-UHFFFAOYSA-N 5-methyl-1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound CC1=NNC(S)=N1 OUZCWDMJTKYHCA-UHFFFAOYSA-N 0.000 description 1
MCAOPHPJGGEBHP-UHFFFAOYSA-N 6,8-dichloro-1-propan-2-yl-[1,2,4]triazolo[3,4-b][1,3]benzothiazole Chemical compound ClC1=CC(Cl)=C2N3C(C(C)C)=NN=C3SC2=C1 MCAOPHPJGGEBHP-UHFFFAOYSA-N 0.000 description 1
JETBHSZJWBBCTF-UHFFFAOYSA-N 6-chloro-1-methyl-[1,2,4]triazolo[3,4-b][1,3]benzothiazole Chemical compound ClC1=CC=C2N3C(C)=NN=C3SC2=C1 JETBHSZJWBBCTF-UHFFFAOYSA-N 0.000 description 1
MCZMXYQZGKDRQQ-UHFFFAOYSA-N 7-chloro-1-methyl-[1,2,4]triazolo[3,4-b][1,3]benzothiazole Chemical compound ClC=1C=CC2=C(N3C(S2)=NN=C3C)C1 MCZMXYQZGKDRQQ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000221785 Erysiphales Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
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 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
229940028332 halog Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
MEXKFCWMWJZDMF-UHFFFAOYSA-N n,n-dibutylacetamide Chemical compound CCCCN(C(C)=O)CCCC MEXKFCWMWJZDMF-UHFFFAOYSA-N 0.000 description 1
DNEJTAGALVCNCG-UHFFFAOYSA-N n-(dimethylamino)carbamothioyl chloride Chemical compound CN(C)NC(Cl)=S DNEJTAGALVCNCG-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
238000010792 warming Methods 0.000 description 1

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Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA78301999A 1974-03-07 1978-04-26 Composes de type 4-(0-halophenyl)-1,2,4-triazole-3-thiol Expired CA1048509A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/449,141 US3937713A (en)	1974-03-07	1974-03-07	Process for the preparation of s-triazolo[3,4-b]benzothiazoles
CA75221381A CA1048506A (fr)	1974-03-07	1975-03-06	Synthese de s-triazolo (3,4-b) benzothiazoles

Publications (1)

Publication Number	Publication Date
CA1048509A true CA1048509A (fr)	1979-02-13

Family

ID=25667852

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA78301998A Expired CA1048539A (fr)	1974-03-07	1978-04-26	Composes de type 1-acyl-4(0-halophenyl) thiosemicarbazide
CA78301999A Expired CA1048509A (fr)	1974-03-07	1978-04-26	Composes de type 4-(0-halophenyl)-1,2,4-triazole-3-thiol

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CA78301998A Expired CA1048539A (fr)	1974-03-07	1978-04-26	Composes de type 1-acyl-4(0-halophenyl) thiosemicarbazide

Country Status (1)

Country	Link
CA (2)	CA1048539A (fr)

1978
- 1978-04-26 CA CA78301998A patent/CA1048539A/fr not_active Expired
- 1978-04-26 CA CA78301999A patent/CA1048509A/fr not_active Expired

Also Published As

Publication number	Publication date
CA1048539A (fr)	1979-02-13

Publication	Publication Date	Title
CA1195325A (fr)	1985-10-15	Derives de l'imidazole, procede de production et preparations pharmaceutiques les contenant
CA1048506A (fr)	1979-02-13	Synthese de s-triazolo (3,4-b) benzothiazoles
L'Abbé et al.	1989	Dimroth rearrangement of 5‐hydrazino‐1, 2, 3‐thiadiazoles
Sasaki et al.	1982	Ring Transformation of 1, 3, 4-Oxadiazole to s-Triazole-Fused Heterocycles. New Synthetic Route for Thiazolo [2, 3-c]-s-triazole and 7H-s-Triazolo [3, 4-b][1, 3, 4] thiadiazine
US4082762A (en)	1978-04-04	4-(2-halophenyl)-1,2,4-triazole-3-thiol compounds
CA1048509A (fr)	1979-02-13	Composes de type 4-(0-halophenyl)-1,2,4-triazole-3-thiol
CN112390725B (zh)	2021-10-29	一种酰胺类化合物的制备方法
US4134914A (en)	1979-01-16	1-Acyl-4-substituted phenyl thiosemicarbazides
CA1302420C (fr)	1992-06-02	Derives de l'indene et methodes pour leur preparation
Dawood et al.	2006	A Convenient Access to Functionalized Pyrazole, Pyrazolyl‐Azole, and Pyrazolo [3, 4‐d] Pyridazine Derivatives
El-Emam et al.	1990	Triazoles and fused triazoles, III: facile and efficient synthesis of 2, 5-disubstituted-s-triazolo [3, 4-b]-1, 3, 4-thiadiazoles
Kojima et al.	1992	Synthesis of indolizines and pyrrolo [2, 1‐b] azoles from 2‐pyridylmagnesium bromide and 2‐lithiated azoles using tris (alkylthio)‐cyclopropenyl cations as a three‐carbon building block
KR790001654B1 (ko)	1979-12-01	S-트리아졸로[3, 4-b] 벤조티아졸류의 제조방법
KR790001653B1 (ko)	1979-12-01	S-트리아졸로[3, 4-b] 벤조티아졸류의 제조방법
EP3541798A1 (fr)	2019-09-25	Procédés de préparation de 4-((6-(2-(2,4-difluorophényl)-1,1-difluoro-2-hydroxy-3-(5-mercapto-1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile
SU470959A3 (ru)	1975-05-15	Способ получени 3-амино- 2-пиразолиновых производных или их солей
US7238719B2 (en)	2007-07-03	Process for producing 1,2,3-Triazole compounds
JP2006188582A (ja)	2006-07-20	新規なピラゾロン化合物、並びにそれを用いたメロシアニン色素
KR790001652B1 (ko)	1979-12-01	S-트리아졸로 [3, 4-b] 벤조티아졸류의 제조방법
Obushak et al.	2003	Synthesis of Heterocycles from the Products of Anionic Arylation of Unsaturated Compounds. 7. Products of Haloarylation of Acrylic Acid and Its Esters in the Synthesis of Benzo [b] thiophene Derivatives
CA1116609A (fr)	1982-01-19	Procede d'obtention de derives du thiazole
Rozhkov et al.	2005	Nucleophilic substitution in the series of (1, 2, 3-triazol-1-yl)-1, 2, 5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles
Talebizadeh et al.	2018	A simple and efficient method for the synthesis of 4-tosyloxazoles from tosylmethyl isocyanide with α-ketoimidoyl chlorides
Britsun et al.	2005	Reaction of 2-Aryl-5-R-5, 6-dihydro-7H-[1, 2, 4]-triazolo [5, 1-b][1, 3] thiazin-7-ones with Aryl Bromomethyl Ketones and Benzyl Bromide
Mohareb et al.	1997	Reaction of 4‐aryl‐3‐thiosemicarbazides with carbon disulfide: A facile synthesis of 2, 3‐dihydrothiazoles and their fused derivatives