Water → N-(3-chloro-4-cyano-2-fluorophenyl)acetamide

HRID 1173644노트

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HRID 1173644 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[C:3]=1[Cl:13].[Cu][C:15]#[N:16].O>CN(C)C=O>[Cl:13][C:3]1[C:4]([F:12])=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[CH:6]=[CH:7][C:2]=1[C:15]#[N:16]

참가 물질

5

반응물 3

HCID 962WaterHCID 23273791N-(4-bromo-3-chloro-2-fluorophenyl)acetamideHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 67105224N-(3-chloro-4-cyano-2-fluorophenyl)acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

A mixture of N-(4-bromo-3-chloro-2-fluorophenyl)acetamide (17.0 g) and copper(I) cyanide (5.88 g) in N,N-dimethylformamide was stirred at 150° C. overnight. After warming to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give N-(3-chloro-4-cyano-2-fluorophenyl)acetamide. Ethanol (250 ml)-concentrated hydrogen chloride (26.6 mL) was added to N-(3-chloro-4-cyano-2-fluorophenyl)acetamide, and the mixture was refluxed overnight. The mixture was ice-cooled, and neutralized with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column, and the obtained solid was washed with hexane to give the title compound as a pale-yellow solid (yield: 7.0 g, 64%).

후처리

  1. temperatureAfter warming to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-97f9963c02c9406a98b65b973bfe3ed9
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834051B2

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