N-bromobutanimide → Ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoate

HRID 906188ノート

反応式

HRID 906188 の反応式
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])#[N:2].[Br:19]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:19][C:12]1[CH:13]=[C:3]([C:1]#[N:2])[C:4]([NH:14][CH2:15][CH:16]([CH3:17])[CH3:18])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 67405767Ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate

生成物 1

HCID 67402604Ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoate収率 72%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
45 °C

実験手順

To a solution of ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate (393 mg, 1.60 mmol) in DMF (10 mL) was added N-bromsuccinimide (284 mg, 1.60 mmol). The mixture was stirred overnight at 45° C. then cooled to room temperature and diluted with water then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (10% ethyl acetate in hexanes) to give ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoate (374 mg, 72.0%) as a yellow solid. MS (EI) for C14H17BrN2O2: 324 (M+).

後処理

  1. temperaturethen cooled to room temperature
  2. extractionthen extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (10% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-2309d0b922894f58a51278575f48ce06
出典データセット
uspto-grants-2011_09
特許番号
US08012956B2

反応ノート

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