Water → 2-Bromo-N-methyl-N-[(4-nitrophenyl)methyl]acetamide

HRID 1451651

반응식

HRID 1451651 반응식
[Br:1][CH2:2][C:3](Br)=[O:4].[CH3:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.O>C(Cl)Cl.C(N(CC)CC)C>[Br:1][CH2:2][C:3]([N:7]([CH3:6])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)=[O:4]

참가 물질

6

반응물 3

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 409440N-methyl-1-(4-nitrophenyl)methanamine

생성물 1

HCID 199744472-Bromo-N-methyl-N-[(4-nitrophenyl)methyl]acetamide수율 104.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

To a solution of bromoacetyl bromide (30 g) in methylene chloride (20 ml) at 0° was added a solution of N-methyl-4-nitrobenzenemethanamine (8.3 g; G. I. Wilson, J. Chem. Soc., 1926, 2461) in methylene chloride (10 ml) and triethylamine (12 ml). The reaction was stirred 5 min. at 0° and then water (20 ml) was added. The methylene chloride layer was dried and evaporated in vacuo. The residue was purified by column chromatography eluting with methylene chloride/methanol (97:3) to give the title compound (15 g) as an oil. NMR includes signals at d 3.1(3H,s,N--CH3); 3.9(2H,s,CH2Br); 4.55(2H,s,Ph--CH2 --N); 7.0-8.3(4H,m,aromatics).

후처리

  1. dry with materialThe methylene chloride layer was dried
  2. customevaporated in vacuo
  3. customThe residue was purified by column chromatography
  4. washeluting with methylene chloride/methanol (97:3)

출처 및 근거

ORD 기록
ord-1a67e430599c4101b9bb2072d5efaa11
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05604237

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