Chloroacetyl chloride → N-[4-Bromo-2-(1-hydroxy-1-phenylethyl)phenyl]-2-chloroacetamide

HRID 1816887Notes

Reaction equation

HRID 1816887 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([OH:11])[CH3:10].[Cl:18][CH2:19][C:20](Cl)=[O:21]>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:20](=[O:21])[CH2:19][Cl:18])=[C:3]([C:9]([OH:11])([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:10])[CH:4]=1

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 688650541-(2-Amino-5-bromophenyl)-1-phenylethanol

Product 1

HCID 68863767N-[4-Bromo-2-(1-hydroxy-1-phenylethyl)phenyl]-2-chloroacetamide

Procedure

Prepared from 1-(2-amino-5-bromophenyl)-1-phenylethanol and chloroacetyl chloride according to the acylation procedure described in example 1. 1H-NMR (DMSO-d6) δ 10.42 (s, 1H), 7.93 (d, J=8.71 Hz, 1H), 7.64 (d, J=1.86 Hz, 1H), 7.52 (dd, J=1.77, 8.71 Hz, 1H), 7.33-7.18 (m, 5H), 6.99 (s, 1H), 4.17 (d, J=14.92 Hz, 1H), 3.99 (d, J=14.98 Hz, 1H), 1.84 (s, 3H); MS (ES) m/z 366/368/370 ([M−H]−, 100%); Anal. Calc. For C16H15BrClNO2: C, 52.13; H, 4.10; N, 3.80. Found: C, 52.18; H, 4.05; N, 3.77.

Sources & evidence

ORD record
ord-5f2891c3001649d49047af9ee839052a
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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