Triethylamine → 3-chloro-N-(3-fluorophenyl)propanamide

HRID 1521637노트

반응식

HRID 1521637 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[Cl:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>ClCCl.O>[Cl:16][CH2:17][CH2:18][C:19]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=1)=[O:20]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 97423-FluoroanilineHCID 693643-Chloropropionyl chloride

생성물 1

HCID 35556953-chloro-N-(3-fluorophenyl)propanamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a stirred solution of 3-fluoroaniline (20 g, 0.180 mol) in dichloromethane (100 mL) was added triethylamine (21.816 g, 0.216 mol) and 3-chloropropanoyl chloride (17.18 mL, 0.180 mol) under cooling condition (0° C.) with constant stirring. Reaction mass was allowed to stir at room temperature for 12 h. The reaction mixture was diluted with water (300 mL) and extracted with dichloromethane (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 7.51-7.48 (d, J=10.4 Hz, 1H), 7.42 (bs, 1H), 7.29-7.24 (dd, J=14.8 Hz, 8.0 Hz, 1H), 7.15-7.13 (d, J=8.0 Hz, 1H), 6.84-6.81 (t, J=6.8 Hz, 1H), 3.89-3.86 (t, J=6.4 Hz, 2H), 2.83-2.80 (t, J=6.4 Hz, 2H). MS (M+1): 201.9.

후처리

  1. customReaction mass
  2. extractionextracted with dichloromethane (4×100 mL)
  3. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-b8a90603582e4bbf9ad7dbb5e9516811
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

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