JPS5978161A - ３−クロロ−１−ホルミル−４−フエニルピロ−ル類の製造方法 - Google Patents
３−クロロ−１−ホルミル−４−フエニルピロ−ル類の製造方法Info
- Publication number
- JPS5978161A JPS5978161A JP18819282A JP18819282A JPS5978161A JP S5978161 A JPS5978161 A JP S5978161A JP 18819282 A JP18819282 A JP 18819282A JP 18819282 A JP18819282 A JP 18819282A JP S5978161 A JPS5978161 A JP S5978161A
- Authority
- JP
- Japan
- Prior art keywords
- water
- pyrroline
- general formula
- adduct
- room temperature
- 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
- 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 title description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims abstract description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000003236 pyrrolines Chemical class 0.000 claims abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 150000003948 formamides Chemical class 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 20
- 239000007864 aqueous solution Substances 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract description 5
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 abstract description 5
- 239000003960 organic solvent Substances 0.000 abstract description 5
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 abstract description 3
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 abstract description 3
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 230000002070 germicidal effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 238000003756 stirring Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- 239000005457 ice water Substances 0.000 description 16
- 238000001816 cooling Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product 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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- 238000006243 chemical reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 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
- 239000002244 precipitate Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000000746 purification Methods 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
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
- 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
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- -1 propatool Chemical compound 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 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
- 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
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 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 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
- YRRQIMILQNHXTB-UHFFFAOYSA-N 3-chloro-4-phenyl-1h-pyrrole Chemical class ClC1=CNC=C1C1=CC=CC=C1 YRRQIMILQNHXTB-UHFFFAOYSA-N 0.000 description 1
- LJDRAKFYYGCAQC-UHFFFAOYSA-N 3-phenyl-1h-pyrrole Chemical class N1C=CC(C=2C=CC=CC=2)=C1 LJDRAKFYYGCAQC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 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
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 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. |
| US06/619,158 US4594429A (en) | 1982-10-28 | 1983-10-21 | Process for producing the 3-chloro-1-formyl-4-phenylpyrroles |
| 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 |
| 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 true JPS5978161A (ja) | 1984-05-04 |
| JPH0261944B2 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 |
|---|---|
| JPH0261944B2 (enrdf_load_stackoverflow) | 1990-12-21 |
| SU1299504A3 (ru) | 1987-03-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108440384B (zh) | 异吲哚酮的三氟甲基羟基化衍生物的制备方法 | |
| JP3663229B2 (ja) | ４−ハロ−２′−ニトロブチロフエノン化合物の製造方法 | |
| JPH0748341A (ja) | ２−クロル−４−メチルスルホニル安息香酸の製造法 | |
| JPS5978161A (ja) | ３−クロロ−１−ホルミル−４−フエニルピロ−ル類の製造方法 | |
| JP2005502701A (ja) | ３−ブロモメチル安息香酸の製造方法 | |
| NO20025652L (no) | Fremgangsmåte for fremstilling av trifluoretoksysubstituerte benzosyrer | |
| JPS6157536A (ja) | ２−ニトロ−４，６−ジクロル−５−エチルフエノ−ルの製造法 | |
| CN106083718B (zh) | 一种异喹啉-1,3,4-三酮衍生物及其制备方法 | |
| JPS597699B2 (ja) | インドリン類の製造方法 | |
| JPH07121931B2 (ja) | ベンゾ〔ｂ〕フラン誘導体 | |
| JPH08208591A (ja) | ２−アミノベンゼンスルホン酸誘導体ならびに２−アミノベンゼンスルホニルクロリド誘導体とその製造法およびその合成中間体としての使用 | |
| JP2535711B2 (ja) | Ｎ−エチル−ヒドロキシルアミン塩酸塩の製法 | |
| JP2706554B2 (ja) | ４―トリフルオロメチルアニリン誘導体及びその製造法 | |
| JP4902976B2 (ja) | フッ素化された１，３−ベンゾジオキサン、その製造及び使用 | |
| US4594429A (en) | Process for producing the 3-chloro-1-formyl-4-phenylpyrroles | |
| JPH0586000A (ja) | ２−アミノ−４−フルオロ安息香酸の製造方法 | |
| JP4956760B2 (ja) | ３−ブロモ安息香酸またはそのアルキルエステルの製造方法 | |
| JPS59130832A (ja) | ４−ハロゲノ−２−クロロ−３−フエニルクロトンアルデヒド | |
| RU1031103C (ru) | Способ получени 9,10-бис-(фенилэтинил)-антрацена и его хлорпроизводного | |
| JPH0261943B2 (enrdf_load_stackoverflow) | ||
| JPS5923314B2 (ja) | 新規ピロ−ル誘導体 | |
| JPS58185559A (ja) | ３−フエニルピロ−ル誘導体の製造方法 | |
| JPS5823668A (ja) | ４−ベンゾイル−５−ヒドロキシピラゾ−ル系化合物の製造方法 | |
| JP2002275167A (ja) | ５−置換オキサゾール化合物の製造方法 | |
| JPH07118239A (ja) | ４−クロロイミダゾール−５−カルバルデヒド誘導体の製造法 |