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

HRID 906188노트

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HRID 906188 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
45 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-2309d0b922894f58a51278575f48ce06
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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