CH527191A - Verfahren zur Herstellung von Pyridinderivaten - Google Patents

Verfahren zur Herstellung von Pyridinderivaten

Info

Publication number: CH527191A
Authority: CH; Switzerland
Prior art keywords: alkali metal; sodium; formula; dihydro; potassium
Prior art date: 1968-08-28

Application number

CH1124969A

Other languages

German (de)

English (en)

Inventor

Guenther Dr Mohr

Alfred Dr Joos

Klemens Dr Schuehrer

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.)

1968-08-28

Filing date

1969-07-23

Publication date

1972-08-31

1969-07-23 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1972-08-31 Publication of CH527191A publication Critical patent/CH527191A/de

Links

229910052708 sodium Inorganic materials 0.000 title claims description 22
239000011734 sodium Substances 0.000 title claims description 22
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 title claims description 21
229910052700 potassium Inorganic materials 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 title description 9
239000011591 potassium Substances 0.000 title description 9
239000000417 fungicide Substances 0.000 title description 2
230000000855 fungicidal effect Effects 0.000 title 1
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims abstract description 38
150000001875 compounds Chemical class 0.000 claims abstract description 21
150000003222 pyridines Chemical class 0.000 claims abstract description 16
239000002253 acid Substances 0.000 claims abstract description 10
239000002168 alkylating agent Substances 0.000 claims abstract description 5
229940100198 alkylating agent Drugs 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 40
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 16
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 claims description 14
-1 alkyl cyanoacetate Chemical compound 0.000 claims description 10
239000013067 intermediate product Substances 0.000 claims description 6
150000001350 alkyl halides Chemical class 0.000 claims description 4
150000008050 dialkyl sulfates Chemical class 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
150000001339 alkali metal compounds Chemical class 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 abstract description 19
150000001340 alkali metals Chemical class 0.000 abstract description 19
150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 18
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract description 11
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000003513 alkali Substances 0.000 description 6
229910001854 alkali hydroxide Inorganic materials 0.000 description 6
239000000047 product Substances 0.000 description 6
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
230000029936 alkylation Effects 0.000 description 5
238000005804 alkylation reaction Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000000126 substance Substances 0.000 description 5
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 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
HRGQEKKNLHJZGZ-UHFFFAOYSA-N 2-methylpropyl 2-cyanoacetate Chemical compound CC(C)COC(=O)CC#N HRGQEKKNLHJZGZ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
229940008406 diethyl sulfate Drugs 0.000 description 2
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical class OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
AOZMBMOAFWUDGX-UHFFFAOYSA-N S1SC(C=C1)C(=O)O.C=C Chemical class S1SC(C=C1)C(=O)O.C=C AOZMBMOAFWUDGX-UHFFFAOYSA-N 0.000 description 1
PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
YQCIWBXEVYWRCW-UHFFFAOYSA-N methane;sulfane Chemical compound C.S YQCIWBXEVYWRCW-UHFFFAOYSA-N 0.000 description 1
ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000010561 standard procedure Methods 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
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)

CH1124969A 1968-08-28 1969-07-23 Verfahren zur Herstellung von Pyridinderivaten CH527191A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19681795241 DE1795241A1 (de)	1968-08-28	1968-08-28	Neue Pyridinderivate und Verfahren zu deren Herstellung

Publications (1)

Publication Number	Publication Date
CH527191A true CH527191A (de)	1972-08-31

Family

ID=5708113

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1124969A CH527191A (de)	1968-08-28	1969-07-23	Verfahren zur Herstellung von Pyridinderivaten

Country Status (9)

Country	Link
AT (1)	AT294092B (cs)
BR (1)	BR6911886D0 (cs)
CH (1)	CH527191A (cs)
CS (1)	CS153049B2 (cs)
DE (1)	DE1795241A1 (cs)
ES (1)	ES370896A1 (cs)
NL (1)	NL6913000A (cs)
RO (1)	RO56102A (cs)
SE (1)	SE350968B (cs)

1968
- 1968-08-28 DE DE19681795241 patent/DE1795241A1/de active Pending
1969
- 1969-07-23 CH CH1124969A patent/CH527191A/de not_active IP Right Cessation
- 1969-08-01 AT AT744669A patent/AT294092B/de not_active IP Right Cessation
- 1969-08-06 RO RO6074069A patent/RO56102A/ro unknown
- 1969-08-19 CS CS573069A patent/CS153049B2/cs unknown
- 1969-08-22 SE SE1168669A patent/SE350968B/xx unknown
- 1969-08-26 NL NL6913000A patent/NL6913000A/xx unknown
- 1969-08-27 ES ES370896A patent/ES370896A1/es not_active Expired
- 1969-08-27 BR BR21188669A patent/BR6911886D0/pt unknown

Also Published As

Publication number	Publication date
ES370896A1 (es)	1971-07-01
AT294092B (de)	1971-11-10
DE1795241A1 (de)	1971-12-30
BR6911886D0 (pt)	1973-02-22
RO56102A (cs)	1974-04-01
SE350968B (cs)	1972-11-13
NL6913000A (cs)	1970-03-03
CS153049B2 (cs)	1974-02-22

Legal Events

Date	Code	Title	Description
1976-02-27	PL	Patent ceased

Publication	Publication Date	Title
AT291228B (de)	1971-07-12	Verfahren zur Herstellung neuer α,α-Dimethyl-ω-phenoxyalkansäuren, ihrer Salze oder Alkylester
DE1543957B1 (de)	1971-02-11	Verfahren zur Herstellung von Bis(hydroxydialkylbenzyl)-sulfiden
DE1817879B2 (de)	1973-12-13	1 (N Athoxycarbonyl N5 thioureido)-2 (N methoxycarbonyl N* thioureido) ben zol, seine Herstellung und seine Ver wendung als Fungicid Ausscheidung aus 1806123
DD149454A5 (de)	1981-07-15	Lepidoptere vertilgende zusammensetzung
DE2240664A1 (de)	1973-03-08	Thiolester von guanidin-substituierten carbonsaeuren
DD140041B1 (de)	1986-05-07	Verfahren zur herstellung von langkettigen n-alkyldimethylmorpholinen
DE2815340C2 (cs)	1988-06-16
DE940827C (de)	1956-03-29	Verfahren zur Herstellung von organischen Arsenverbindungen
DE1795241A1 (de)	1971-12-30	Neue Pyridinderivate und Verfahren zu deren Herstellung
DE1192647B (de)	1965-05-13	Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphonsaeureestern
CH513849A (de)	1971-10-15	Verfahren zur Herstellung von Pyrrolinverbindungen
AT206444B (de)	1959-11-25	Verfahren zur Herstellung von neuen Pyridazinderivaten
DD139577A1 (de)	1980-01-09	Verfahren zur herstellung von n-sulfoalkyl-substituierten aminen
AT201602B (de)	1959-01-10	Verfahren zur Herstellung neuer Sulfonamide
AT251565B (de)	1967-01-10	Verfahren zur Herstellung von neuen Carbonsäuren
AT214456B (de)	1961-04-10	Verfahren zur Herstellung der neuen Verbindung Dimethyl-1, 2-dibrom-2, 2-dichloräthylphosphat
AT222103B (de)	1962-07-10	Verfahren zur Herstellung von 2-trans-β-Jonylidenessigsäure
AT258916B (de)	1967-12-27	Verfahren zur Herstellung von neuen Alkyl-3-amino-5-chlor-6-X-pyrazinoaten
AT162936B (de)	1949-04-25	Verfahren zur Herstellung von neuen substituierten 2,4-Diamino-1,3,5-triazinen
AT220149B (de)	1962-03-12	Verfahren zur Herstellung von Aryloxymethyl-2-oxazolidinonen
DE1925423C (de)	1972-09-07	2,2-Dimethyl-omega-aryloxy alkansäuren und deren Derivate
AT263023B (de)	1968-07-10	Verfahren zur Herstellung von neuen Phenothiazinderivaten und ihren Salzen
AT214454B (de)	1961-04-10	Verfahren zur Herstellung neuer Phosphinsäurederivate
AT234105B (de)	1964-06-10	Verfahren zur Herstellung von 4-Methyl-6-isobutenyl-pyron-(2)
DE1543957C (de)	1971-09-16	Verfahren zur Herstellung von Bishydroxy dialkylbenzyl) sulfiden Ausscheidung aus 1242617