JPH0261944B2 - - Google Patents
Info
- Publication number
- JPH0261944B2 JPH0261944B2 JP18819282A JP18819282A JPH0261944B2 JP H0261944 B2 JPH0261944 B2 JP H0261944B2 JP 18819282 A JP18819282 A JP 18819282A JP 18819282 A JP18819282 A JP 18819282A JP H0261944 B2 JPH0261944 B2 JP H0261944B2
- Authority
- JP
- Japan
- Prior art keywords
- solution
- pyrroline
- water
- general formula
- stirring
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 8
- 150000003236 pyrrolines Chemical class 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 150000003948 formamides Chemical class 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 21
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000005457 ice water Substances 0.000 description 16
- 238000001816 cooling Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000001632 sodium acetate Substances 0.000 description 7
- 235000017281 sodium acetate Nutrition 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- FSPXZKAEHGXEHN-RJRFIUFISA-N (z)-2,4-dichlorobut-2-enal Chemical compound ClC\C=C(/Cl)C=O FSPXZKAEHGXEHN-RJRFIUFISA-N 0.000 description 3
- FPDUKQMWXINZQU-UHFFFAOYSA-N 3-chloro-4-(2,3-dichlorophenyl)pyrrole-1-carbaldehyde Chemical compound ClC1=CN(C=O)C=C1C1=CC=CC(Cl)=C1Cl FPDUKQMWXINZQU-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000003233 pyrroles Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- SIIZTCVAFPKFNN-UHFFFAOYSA-N 3-chloro-4-phenylpyrrole-1-carbaldehyde Chemical class ClC1=CN(C=O)C=C1C1=CC=CC=C1 SIIZTCVAFPKFNN-UHFFFAOYSA-N 0.000 description 2
- NEYNPUSYSKSQRG-UHFFFAOYSA-N 4,4,4-trichlorobutanal Chemical compound ClC(Cl)(Cl)CCC=O NEYNPUSYSKSQRG-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
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-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
- BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical compound NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 1
- CKUDAFXOXRKRIY-UHFFFAOYSA-N 3-chloro-4-(2-chlorophenyl)pyrrole-1-carbaldehyde Chemical compound ClC1=CN(C=O)C=C1C1=CC=CC=C1Cl CKUDAFXOXRKRIY-UHFFFAOYSA-N 0.000 description 1
- NQZDTSRBZCITBB-UHFFFAOYSA-N 3-chloro-4-(2-nitrophenyl)pyrrole-1-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CN(C=O)C=C1Cl NQZDTSRBZCITBB-UHFFFAOYSA-N 0.000 description 1
- PZBDGIBNEUROLB-UHFFFAOYSA-N 3-chloro-4-[2-(trifluoromethyl)phenyl]pyrrole-1-carbaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C1=CN(C=O)C=C1Cl PZBDGIBNEUROLB-UHFFFAOYSA-N 0.000 description 1
- YRRQIMILQNHXTB-UHFFFAOYSA-N 3-chloro-4-phenyl-1h-pyrrole Chemical class ClC1=CNC=C1C1=CC=CC=C1 YRRQIMILQNHXTB-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- -1 N-methylformanilide Chemical class 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 150000008060 phenylpyrroles Chemical class 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18819282A JPS5978161A (ja) | 1982-10-28 | 1982-10-28 | ３−クロロ−１−ホルミル−４−フエニルピロ−ル類の製造方法 |
| EP19830903404 EP0134245A4 (en) | 1982-10-28 | 1983-10-21 | PROCESS FOR THE PREPARATION OF 3-CHLORO-1-FORMYL-4-PHENYL-PYRROLES. |
| PCT/JP1983/000371 WO1984001773A1 (en) | 1982-10-28 | 1983-10-21 | Process for preparing 3-chloro-1-formyl-4-phenyl-pyrroles |
| HU891680A HU202491B (en) | 1982-10-28 | 1983-10-21 | Process for producing pyrroline derivatives |
| US06/619,158 US4594429A (en) | 1982-10-28 | 1983-10-21 | Process for producing the 3-chloro-1-formyl-4-phenylpyrroles |
| SU843754201A SU1299504A3 (ru) | 1982-10-28 | 1984-06-25 | Способ получени производных 3-хлор-1-формил-4-фенилпирролов |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18819282A JPS5978161A (ja) | 1982-10-28 | 1982-10-28 | ３−クロロ−１−ホルミル−４−フエニルピロ−ル類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5978161A JPS5978161A (ja) | 1984-05-04 |
| JPH0261944B2 true JPH0261944B2 (enrdf_load_stackoverflow) | 1990-12-21 |
Family
ID=16219376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18819282A Granted JPS5978161A (ja) | 1982-10-28 | 1982-10-28 | ３−クロロ−１−ホルミル−４−フエニルピロ−ル類の製造方法 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5978161A (enrdf_load_stackoverflow) |
| SU (1) | SU1299504A3 (enrdf_load_stackoverflow) |
-
1982
- 1982-10-28 JP JP18819282A patent/JPS5978161A/ja active Granted
-
1984
- 1984-06-25 SU SU843754201A patent/SU1299504A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| SU1299504A3 (ru) | 1987-03-23 |
| JPS5978161A (ja) | 1984-05-04 |
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