Triethylamine → 2-bromo-N-cyclopropyl-N-phenyl-acetamide

HRID 343143노트

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HRID 343143 반응식
[CH:1]1([NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.CCN(CC)CC.[Br:18][CH2:19][C:20](Br)=[O:21]>C(Cl)Cl>[Br:18][CH2:19][C:20]([N:4]([CH:1]1[CH2:3][CH2:2]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:21]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 7016287N-Cyclopropylaniline

생성물 1

HCID 107060812-bromo-N-cyclopropyl-N-phenyl-acetamide수율 54.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

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온도
0 °C

실험 절차

To a stirred solution of 908 mg (6.83 mmol) Cyclopropyl-phenyl-amine (Kang, Sung, Kim, J. Chem. Soc., Chem. Commun., 1987, 897-898) and 690 mg (6.83 mmol, 1 equiv) Et3N in 10 mL DCM is added 1.38 g (6.83 mmol, 1 equiv) Bromoacetyl bromide in 4 mL DCM dropwise over 15 minutes at 0° C. The reaction mixture is stirred 3 h at 0° C., diluted with 30 mL DCM, washed with 1N HCl (30 mL), dried (MgSO4), and concentrated in vacuo. The crude product is purified by flash chromatography on 30 g silica gel eluted successively with EtOAc/Hexanes (1:9, 100 mL), (3:17, 300 mL). Appropriate fractions were combined and concentrated in vacuo to give 948 mg (3.73 mmol) of 2-Bromo-N-cyclopropyl-N-phenyl-acetamide as an amber oil: 1H NMR (CDCl3, 300 MHz) δ7.39 (m, 3H), 7.15 (m, 2H), 3.62 (s, br, 2H), 3.24 (m, 1H), 0.83 (m, 2H), 0.52 (m, 2H); TLC Rf =0.18 (EtOAc/Hexanes, 3:17).

후처리

  1. washwashed with 1N HCl (30 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product is purified by flash chromatography on 30 g silica gel
  5. washeluted successively with EtOAc/Hexanes (1:9, 100 mL), (3:17, 300 mL)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a17aee312b504406b89bd77c9faa1ca8
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859007

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