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

HRID 1929456Notes

Reaction equation

HRID 1929456 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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. There were obtained 9.62 g (86% of theory) of (RS)-N-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide as a light brown oil. Mass (calculated) C11H13BrClNO2 [306.589]; (found) [M+H]+=306, [M+2-H]+=308.

Workup

  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

Sources & evidence

ORD record
ord-c044f58df3d64d419f33edc6f0e8fb99
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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