JPH0322381B2 - - Google Patents
Info
- Publication number
- JPH0322381B2 JPH0322381B2 JP6984882A JP6984882A JPH0322381B2 JP H0322381 B2 JPH0322381 B2 JP H0322381B2 JP 6984882 A JP6984882 A JP 6984882A JP 6984882 A JP6984882 A JP 6984882A JP H0322381 B2 JPH0322381 B2 JP H0322381B2
- Authority
- JP
- Japan
- Prior art keywords
- hours
- ammonia
- general formula
- reaction
- yield
- 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.)
- Expired
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NZYIPVQQHZWTRB-UHFFFAOYSA-N 2,2,4-trichloro-3-(2,3-dichlorophenyl)butanal Chemical compound O=CC(Cl)(Cl)C(CCl)C1=CC=CC(Cl)=C1Cl NZYIPVQQHZWTRB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- FSPXZKAEHGXEHN-RJRFIUFISA-N (z)-2,4-dichlorobut-2-enal Chemical compound ClC\C=C(/Cl)C=O FSPXZKAEHGXEHN-RJRFIUFISA-N 0.000 description 1
- VNJOVWYGVMZBNB-UHFFFAOYSA-N 2,2,4-trichloro-3-(2-chlorophenyl)butanal Chemical compound O=CC(Cl)(Cl)C(CCl)C1=CC=CC=C1Cl VNJOVWYGVMZBNB-UHFFFAOYSA-N 0.000 description 1
- GABOSZQDASEIMX-UHFFFAOYSA-N 2,2,4-trichloro-3-(2-nitrophenyl)butanal Chemical compound [O-][N+](=O)C1=CC=CC=C1C(CCl)C(Cl)(Cl)C=O GABOSZQDASEIMX-UHFFFAOYSA-N 0.000 description 1
- UMKXGODCJYHDSF-UHFFFAOYSA-N 2,2,4-trichloro-3-phenylbutanal Chemical compound O=CC(Cl)(Cl)C(CCl)C1=CC=CC=C1 UMKXGODCJYHDSF-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- 150000005358 3-phenylpyrroles Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000005695 dehalogenation reaction Methods 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
- 238000000605 extraction Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000008060 phenylpyrroles Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57069848A JPS58185559A (ja) | 1982-04-26 | 1982-04-26 | ３−フエニルピロ−ル誘導体の製造方法 |
| US06/485,910 US4471126A (en) | 1982-04-26 | 1983-04-18 | Method for the production of 3-phenylpyrrole |
| KR1019830001722A KR860001335B1 (ko) | 1982-04-26 | 1983-04-23 | 3-페닐피롤 유도체의 제조방법 |
| EP83200592A EP0092890A1 (en) | 1982-04-26 | 1983-04-25 | Method for the production of 3-phenylpyrrole derivatives |
| ES521830A ES521830A0 (es) | 1982-04-26 | 1983-04-25 | Un metodo para la produccion de derivados de 3-fenilpirrol. |
| HU831433A HU190087B (en) | 1982-04-26 | 1983-04-26 | Process for preparing 3-phenyl-pyrrole derivatives |
| HU854800A HU193454B (en) | 1982-04-26 | 1983-04-26 | Process for producing 3-phenyl-butyraldehyde derivatives |
| IL68519A IL68519A (en) | 1982-04-26 | 1983-04-28 | Production of 3-phenylpyrrole derivatives,and novel 2,4-dichloro-3-phenylbutyraldehyde intermediates therefor |
| SU833657406A SU1225479A3 (ru) | 1982-04-26 | 1983-10-31 | Способ получени альдегидов |
| ES528633A ES528633A0 (es) | 1982-04-26 | 1984-01-02 | Un metodo para la preparacion de nuevos derivados de fenilbutilaldehido |
| US06/615,328 US4532363A (en) | 1982-04-26 | 1984-05-30 | Phenylbutyraldehydes |
| KR8606472A KR860001388B1 (en) | 1982-04-26 | 1986-08-05 | Process for the preparation of intermedium for the 3-phenyl pyrrole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57069848A JPS58185559A (ja) | 1982-04-26 | 1982-04-26 | ３−フエニルピロ−ル誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58185559A JPS58185559A (ja) | 1983-10-29 |
| JPH0322381B2 true JPH0322381B2 (enExample) | 1991-03-26 |
Family
ID=13414633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57069848A Granted JPS58185559A (ja) | 1982-04-26 | 1982-04-26 | ３−フエニルピロ−ル誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58185559A (enExample) |
-
1982
- 1982-04-26 JP JP57069848A patent/JPS58185559A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58185559A (ja) | 1983-10-29 |
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