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

HRID 593334ノート

反応式

HRID 593334 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c703ef598084affb9ad8ae2455fc504
出典データセット
uspto-grants-2016_01
特許番号
US09242943B2

反応ノート

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