Chloroacetyl chloride → N-[4-bromo-2-(1-hydroxyethyl)phenyl]-2-chloroacetamide

HRID 1816884Notes

Reaction equation

HRID 1816884 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH:9]([OH:11])[CH3:10].[Cl:12][CH2:13][C:14](Cl)=[O:15]>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:14](=[O:15])[CH2:13][Cl:12])=[C:3]([CH:9]([OH:11])[CH3:10])[CH:4]=1

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 688650521-(2-Amino-5-bromophenyl)ethan-1-ol

Product 1

HCID 68863694N-[4-bromo-2-(1-hydroxyethyl)phenyl]-2-chloroacetamide

Procedure

Prepared by from 1-(2-amino-5-bromo-phenyl)-ethanol and chloroacetyl chloride generally according to the procedure described in Example 1. 1H-NMR (DMSO-d6) δ 10.11 (s, 1H), 7.64 (d, J=8.63 Hz, 1H), 7.57 (d, J=2.31 Hz, 1H), 7.44 (dd, J=2.34, 8.57 Hz, 1H), 5.77 (d, J=3.88 Hz, 1H), 4.93-4.89 (m, 1H), 4.35, (s, 2H), 1.31 (d, J=6.45 Hz, 3H); MS (ES) m/z 290/292/294 ([M−H]−, 100%).

Sources & evidence

ORD record
ord-0c37ff50e4914b70912b6a635d275672
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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