Chloroacetyl chloride → N-[1-(3-Bromophenyl)-2-hydroxy-1-methylethyl]-2-chloroacetamide

HRID 593334노트

반응식

HRID 593334 반응식
[NH2:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.[Cl:20][CH2:21][C:22](Cl)=[O:23]>C(#N)C>[Br:12][C:8]1[CH:7]=[C:6]([C:2]([NH:1][C:22](=[O:23])[CH2:21][Cl:20])([CH3:5])[CH2:3][OH:4])[CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 532566942-Amino-2-(3-bromophenyl)propan-1-ol

생성물 1

HCID 58155284N-[1-(3-Bromophenyl)-2-hydroxy-1-methylethyl]-2-chloroacetamide수율 87.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of crude (RS)-2-amino-2-(3-bromo-phenyl)-propan-1-ol (8.38 g, 36 mmol) and triethylamine (6.08 ml, 44 mmol) in acetonitrile (140 ml) was treated dropwise at −2° C. with chloroacetylchloride (3.25 ml, 40 mmol). After complete addition, the orange colored solution was left to warm to room temperature and stirring was continued for 2 h. For the workup, to the reaction was added silica gel (10 g) and it was evaporated at reduced pressure, thereafter, it was purified by chromatography on silica gel using a gradient of dichloromethane/methanol=100/0 to 90/10 as the eluent. 9.62 g (86%) of (RS)-N-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide were obtained as a light brown oil. Mass (calculated) C11H13BrClNO2 [306.589]; (found) [M+H]+=306, 308.

후처리

  1. additionAfter complete addition
  2. waitthe orange colored solution was left
  3. additionFor the workup, to the reaction was added silica gel (10 g) and it
  4. customwas evaporated at reduced pressure
  5. customit was purified by chromatography on silica gel using a gradient of dichloromethane/methanol=100/0 to 90/10 as the eluent

출처 및 근거

ORD 기록
ord-9c703ef598084affb9ad8ae2455fc504
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242943B2

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