CA1273345A - Procede pour la production de 3-phenyl -4-cyanopyrroles - Google Patents

Procede pour la production de 3-phenyl -4-cyanopyrroles

Info

Publication number: CA1273345A
Authority: CA; Canada
Prior art keywords: reaction; mol; compound; mixture; added
Prior art date: 1986-01-17
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 - Lifetime

Application number

CA000499772A

Other languages

English (en)

Inventor

Yoshikazu Genda

Yoshiji Sugita

Yoshiaki Miyazaki

Hiroyuki Muro

Kiyoharu Nakayama

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.)

Nippon Soda Co Ltd

Original Assignee

Nippon Soda Co Ltd

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.)

1986-01-17

Filing date

1986-01-17

Publication date

1990-08-28

1986-01-17 Application filed by Nippon Soda Co Ltd filed Critical Nippon Soda Co Ltd

1986-01-17 Priority to CA000499772A priority Critical patent/CA1273345A/fr

1990-08-28 Application granted granted Critical

1990-08-28 Publication of CA1273345A publication Critical patent/CA1273345A/fr

2007-08-28 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 15
238000004519 manufacturing process Methods 0.000 title claims abstract description 8
BMMCNKYHQAKJBN-UHFFFAOYSA-N 4-phenyl-1h-pyrrole-3-carbonitrile Chemical class N#CC1=CNC=C1C1=CC=CC=C1 BMMCNKYHQAKJBN-UHFFFAOYSA-N 0.000 title description 8
238000006243 chemical reaction Methods 0.000 claims abstract description 30
150000001875 compounds Chemical class 0.000 claims abstract description 25
125000001424 substituent group Chemical group 0.000 claims abstract description 13
-1 methylenedioxy Chemical group 0.000 claims abstract description 9
230000002411 adverse Effects 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000002367 halogens Chemical class 0.000 claims abstract description 5
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
150000001732 carboxylic acid derivatives Chemical group 0.000 claims abstract description 3
125000004185 ester group Chemical group 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
230000000694 effects Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
239000000203 mixture Substances 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000013078 crystal Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002904 solvent Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
238000011282 treatment Methods 0.000 description 4
CDUQMGQIHYISOP-RMKNXTFCSA-N (e)-2-cyano-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C\C1=CC=CC=C1 CDUQMGQIHYISOP-RMKNXTFCSA-N 0.000 description 3
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 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
125000005233 alkylalcohol group Chemical group 0.000 description 3
OHUDHPKMAJDBPI-UHFFFAOYSA-N isocyanomethylsulfonylbenzene Chemical compound [C-]#[N+]CS(=O)(=O)C1=CC=CC=C1 OHUDHPKMAJDBPI-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
SADKTSLRGYYBOS-UHFFFAOYSA-N 1-chloro-4-(isocyanomethylsulfonyl)benzene Chemical compound ClC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 SADKTSLRGYYBOS-UHFFFAOYSA-N 0.000 description 2
BQMPGKPTOHKYHS-UHFFFAOYSA-N 1h-pyrrole-2-carbonitrile Chemical compound N#CC1=CC=CN1 BQMPGKPTOHKYHS-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
HSQGMTRYSIHDAC-UHFFFAOYSA-N leucyl-alanine Chemical compound CC(C)CC(N)C(=O)NC(C)C(O)=O HSQGMTRYSIHDAC-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
DMACYVMZKYRYSL-UHFFFAOYSA-N 2-cyano-3-(3,4-dimethoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(C=C(C#N)C(O)=O)C=C1OC DMACYVMZKYRYSL-UHFFFAOYSA-N 0.000 description 1
YYLUJSBONROLKZ-UHFFFAOYSA-N 2-cyano-3-(4-cyanophenyl)prop-2-enoic acid Chemical compound OC(=O)C(C#N)=CC1=CC=C(C#N)C=C1 YYLUJSBONROLKZ-UHFFFAOYSA-N 0.000 description 1
CDUQMGQIHYISOP-UHFFFAOYSA-N 2-cyano-3-phenylprop-2-enoic acid Chemical class OC(=O)C(C#N)=CC1=CC=CC=C1 CDUQMGQIHYISOP-UHFFFAOYSA-N 0.000 description 1
RNBCQLCYZIHPON-UHFFFAOYSA-N 3-(4-bromophenyl)-2-methylprop-2-enal Chemical compound O=CC(C)=CC1=CC=C(Br)C=C1 RNBCQLCYZIHPON-UHFFFAOYSA-N 0.000 description 1
GEWCXMLSRUQIDQ-UHFFFAOYSA-N 4-(2-chlorophenyl)-1h-pyrrole-3-carbonitrile Chemical compound ClC1=CC=CC=C1C1=CNC=C1C#N GEWCXMLSRUQIDQ-UHFFFAOYSA-N 0.000 description 1
JWRQPIFEFRGLSE-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1h-pyrrole-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CNC=C1C#N JWRQPIFEFRGLSE-UHFFFAOYSA-N 0.000 description 1
CJDIWEZPIAEWNK-UHFFFAOYSA-N 4-(4-cyanophenyl)-1h-pyrrole-3-carbonitrile Chemical compound N#CC1=CNC=C1C1=CC=C(C#N)C=C1 CJDIWEZPIAEWNK-UHFFFAOYSA-N 0.000 description 1
HZLGVCAVFBNSGW-UHFFFAOYSA-N C(#N)OC(C(=O)O)=C(C1=CC=CC=C1)Cl Chemical compound C(#N)OC(C(=O)O)=C(C1=CC=CC=C1)Cl HZLGVCAVFBNSGW-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000012770 industrial material Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Landscapes

Pyrrole Compounds (AREA)

CA000499772A 1986-01-17 1986-01-17 Procede pour la production de 3-phenyl -4-cyanopyrroles Expired - Lifetime CA1273345A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000499772A CA1273345A (fr)	1986-01-17	1986-01-17	Procede pour la production de 3-phenyl -4-cyanopyrroles

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000499772A CA1273345A (fr)	1986-01-17	1986-01-17	Procede pour la production de 3-phenyl -4-cyanopyrroles

Publications (1)

Publication Number	Publication Date
CA1273345A true CA1273345A (fr)	1990-08-28

Family

ID=4132289

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000499772A Expired - Lifetime CA1273345A (fr)	1986-01-17	1986-01-17	Procede pour la production de 3-phenyl -4-cyanopyrroles

Country Status (1)

Country	Link
CA (1)	CA1273345A (fr)

1986
- 1986-01-17 CA CA000499772A patent/CA1273345A/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2007-08-28	MKEX	Expiry

Publication	Publication Date	Title
US4680413A (en)	1987-07-14	Process for the production of 3-phenyl-4-cyanopyrroles
KR960001913B1 (ko)	1996-02-06	3-시아노-4-아릴-피롤의 제조방법
CA1273345A (fr)	1990-08-28	Procede pour la production de 3-phenyl -4-cyanopyrroles
NO166712B (no)	1991-05-21	Fremgangsmaate ved fremstilling av pyrrolidonderivater.
WO2021209269A1 (fr)	2021-10-21	Procédé de préparation de composés énamine substitués
US6329536B1 (en)	2001-12-11	Stereoselective process for producing nitro compounds
CN101410386B (zh)	2013-07-24	2-链烯基-3-氨基噻吩衍生物及其制备方法
KR100424341B1 (ko)	2004-03-24	1-메틸인다졸-3-카르복실산의 제조방법
WO2021175959A1 (fr)	2021-09-10	Procédé de préparation de carboxylates et d'amides d'acide 5-chloro-3-alkylsulfanyl-pyridine-2-carboxylique
KR20050057429A (ko)	2005-06-16	중간체의 제조 방법
KR100448640B1 (ko)	2004-11-16	페닐프로피온산 유도체의 제조방법
EP1807401B1 (fr)	2010-07-07	Procede de preparation de phenyl 2-pyrimidinyl cetones et leurs nouveaux intermediaires
US5514811A (en)	1996-05-07	Process for synthesizing 4-halo-5-(hydroxymethyl) imidazole compounds
US4071684A (en)	1978-01-31	Process for producing 3-substituted 1,2,4-triazines
US6057477A (en)	2000-05-02	Metal salt catalyzed process to oxazolines and subsequent formation of chloroketones
KR100352924B1 (ko)	2002-09-16	5-아미노피라졸-4-카르복시산에스테르유도체 및 그 제조방법
JP3066594B2 (ja)	2000-07-17	アニリン誘導体及びその製造法
KR19990015053A (ko)	1999-03-05	2-(4-할로메틸페닐)프로피온산의 제조방법
US4147876A (en)	1979-04-03	Easily hydrolyzable esters of 4-(2-carboxyethyl)phenyl trans-4-aminomethylcyclohexanecarboxylate and process of use
JP3110154B2 (ja)	2000-11-20	３（２ｈ）−ピリダジノン誘導体の製造方法
EP4323332A1 (fr)	2024-02-21	Procédé de préparation de composés énamine substitués
US4924001A (en)	1990-05-08	Process for preparing 5-cyano-4, 5-dihydro-3,4-dicarboxypyrazole derivatives
JPH06128262A (ja)	1994-05-10	４，５−ジヒドロ［１，２，４］トリアゾロ［４，３−ａ］キノキサリン誘導体の製造方法
JPH01153673A (ja)	1989-06-15	２−アシルシクロヘキサン誘導体およびその製造法
CA2138065A1 (fr)	1995-06-16	Procede d'obtention du 5-aminodihydropyrrole, son intermediaire et procede d'obtention de cet intermediaire