Pyrrole → (2-Chloro-3-nitrophenyl)-1H-pyrrol-1-ylmethanone

HRID 895158노트

반응식

HRID 895158 반응식
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1)=[O:6]

참가 물질

8

반응물 4

HCID 8027PyrroleHCID 8471TriethylamineHCID 198702-Chloro-3-nitrobenzoic acidHCID 24386Thionyl Chloride

생성물 1

HCID 22385748(2-Chloro-3-nitrophenyl)-1H-pyrrol-1-ylmethanone수율 97%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

2-Chloro-3-nitrobenzoic acid (2 g, 10.0 mmol) and thionyl chloride (30 ml) were mixed at room temperature, and 4-dimethylaminopyridine (122 mg, 1.00 mmol) was added. The reaction mixture was refluxed for 12 hours and then concentrated to give a crude acid chloride. The acid chloride mentioned above was added to a solution of pyrrole (3.5 ml, 50.0 mmol) and triethylamine (7.0 ml, 50.0 mmol) in methylene chloride (80 ml) at room temperature. The reaction mixture was stirred at the same temperature for 6 hours and diluted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, filtered, and concentrated to give a crude compound. The crude compound was purified by silica gel column chromatography (hexane:ethyl acetate, 1:0-7:3) to give the title compound (2.43 g) as a yellow oil.

후처리

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. concentrationconcentrated
  3. customto give a crude acid chloride
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude compound
  9. customThe crude compound was purified by silica gel column chromatography (hexane:ethyl acetate, 1:0-7:3)

출처 및 근거

ORD 기록
ord-89145b683fe949b1ac2ffea1169a32ad
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06914062B2

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