Aniline → 3-chloro-N-phenylpropanamide

HRID 1521617

반응식

HRID 1521617 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][CH2:9][CH2:10][C:11](Cl)=[O:12]>ClCCl.O>[Cl:8][CH2:9][CH2:10][C:11]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:12]

참가 물질

5

반응물 2

HCID 6115AnilineHCID 693643-Chloropropionyl chloride

생성물 1

HCID 2404043-chloro-N-phenylpropanamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of aniline (40 g, 0.429 mol) in dichloromethane (500 mL) cooled at 0° C., was added 3-chloropropanoyl chloride (49.1 mL, 0.515 mol) drop wise with constant stirring. Reaction mass was allowed to stir at room temperature for 2 h. The reaction mixture was diluted with water (500 mL) and extracted with dichloromethane (4×500 mL). The combined organic layer was washed with saturated sodium bicarbonate solution, saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ 10.01 (s, 1H), 7.58-7.56 (d, J=8 Hz, 2H), 7.30-7.26 (t, J=8 Hz, 2H), 7.05-7.01 (t, J=7.6 Hz, 1H), 3.88-3.85 (t, J=6.4 Hz, 2H), 2.82-2.81 (t, J=6.0 Hz, 2H). MS (M+1): 184.1.

후처리

  1. customReaction mass
  2. extractionextracted with dichloromethane (4×500 mL)
  3. washThe combined organic layer was washed with saturated sodium bicarbonate solution, saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-ab972f7b25a7439b90df915f0077ae29
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

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