Water → 4-Chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester

HRID 405757노트

반응식

HRID 405757 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][N:7]([CH:10]([F:12])[F:11])[N:6]=1)=[O:4].[Cl:13]N1C(=O)CCC1=O.O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:9]([Cl:13])=[CH:8][N:7]([CH:10]([F:12])[F:11])[N:6]=1)=[O:4]

참가 물질

5

반응물 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 57497167Methyl 1-(difluoromethyl)-1H-pyrazole-3-carboxylate

생성물 1

HCID 574758834-Chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

A mixture of 1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester (535 mg, 3 mmol) and N-chloro-succinimide (1.22 g, 9.1 mmol) in N,N-dimethylformamide (5 ml) was heated at 50° C. overnight. The reaction mixture was cooled, poured into water (20 ml), then extracted with ethyl acetate. The organic layer was separated, washed with water, dried over sodium sulphate, finally evaporated at reduced pressure. The yellowish crude material was purified by chromatography on silica gel using a 3:1-mixture of cyclohexane and ethyl acetate as the eluent. The 4-chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester was obtained as a white solid (540 mg, 84% of theory). MS (ISP): m/z=209.9 [M]+.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. customfinally evaporated at reduced pressure
  7. customThe yellowish crude material was purified by chromatography on silica gel using a 3

출처 및 근거

ORD 기록
ord-8cd8fbdd76ac413b901b3c73c233cd69
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754075B2

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