JPS6130571A - ３−フエニル−４−シアノピロ−ル類の製造方法 - Google Patents
３−フエニル−４−シアノピロ−ル類の製造方法Info
- Publication number
- JPS6130571A JPS6130571A JP59150619A JP15061984A JPS6130571A JP S6130571 A JPS6130571 A JP S6130571A JP 59150619 A JP59150619 A JP 59150619A JP 15061984 A JP15061984 A JP 15061984A JP S6130571 A JPS6130571 A JP S6130571A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- lower alkyl
- tosylmethyl isocyanide
- reaction
- Prior art date
- 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.)
- Granted
Links
- BMMCNKYHQAKJBN-UHFFFAOYSA-N 4-phenyl-1h-pyrrole-3-carbonitrile Chemical compound N#CC1=CNC=C1C1=CC=CC=C1 BMMCNKYHQAKJBN-UHFFFAOYSA-N 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000003233 pyrroles Chemical class 0.000 claims description 6
- 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 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 abstract description 10
- -1 methylenedioxy Chemical group 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- 239000005749 Copper compound Substances 0.000 abstract description 2
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001880 copper compounds Chemical class 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract description 2
- 230000000087 stabilizing effect Effects 0.000 abstract description 2
- 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 abstract 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 abstract 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 abstract 1
- 229940112669 cuprous oxide Drugs 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 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 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- WLKDAZQHOLJYQE-UHFFFAOYSA-N 2-cyano-3-(2,3-dichlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C(C#N)=CC1=CC=CC(Cl)=C1Cl WLKDAZQHOLJYQE-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
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229960004643 cupric oxide Drugs 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003657 drainage water Substances 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- HSQGMTRYSIHDAC-UHFFFAOYSA-N leucyl-alanine Chemical compound CC(C)CC(N)C(=O)NC(C)C(O)=O HSQGMTRYSIHDAC-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59150619A JPS6130571A (ja) | 1984-07-20 | 1984-07-20 | ３−フエニル−４−シアノピロ−ル類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59150619A JPS6130571A (ja) | 1984-07-20 | 1984-07-20 | ３−フエニル−４−シアノピロ−ル類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6130571A true JPS6130571A (ja) | 1986-02-12 |
| JPH0432064B2 JPH0432064B2 (enrdf_load_stackoverflow) | 1992-05-28 |
Family
ID=15500824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59150619A Granted JPS6130571A (ja) | 1984-07-20 | 1984-07-20 | ３−フエニル−４−シアノピロ−ル類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6130571A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960789A (en) * | 1987-11-09 | 1990-10-02 | Bayer Aktiengesellschaft | 3-cyano-4-phenyl-pyrroles as fungicides |
| WO1991005769A1 (en) * | 1989-10-17 | 1991-05-02 | Nippon Soda Co., Ltd. | Novel pyrrole monomer, process for preparing the same, and functional polymer film |
-
1984
- 1984-07-20 JP JP59150619A patent/JPS6130571A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960789A (en) * | 1987-11-09 | 1990-10-02 | Bayer Aktiengesellschaft | 3-cyano-4-phenyl-pyrroles as fungicides |
| WO1991005769A1 (en) * | 1989-10-17 | 1991-05-02 | Nippon Soda Co., Ltd. | Novel pyrrole monomer, process for preparing the same, and functional polymer film |
| US5278295A (en) * | 1989-10-17 | 1994-01-11 | Nippon Soda Co., Ltd. | Pyrrole monomer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0432064B2 (enrdf_load_stackoverflow) | 1992-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |