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

HRID 1967316ノート

反応式

HRID 1967316 の反応式
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]

参加物

5

反応物 3

HCID 962WaterHCID 23273791N-(4-bromo-3-chloro-2-fluorophenyl)acetamideHCID 178418546HCID 178418546、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

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 methyl 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%).

後処理

  1. temperatureAfter warming to room temperature
  2. extractionthe mixture was extracted with methyl 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

出典と根拠

ORDレコード
ord-dfa8521e14bb445d867760aa91208eb7
出典データセット
uspto-grants-2013_04
特許番号
US08420694B2

反応ノート

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