Chloroacetyl chloride → N-[4-Bromo-2-(1-hydroxy-1-methyl-ethyl)-phenyl]-2-chloro-acetamide

HRID 1816878Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([OH:12])([CH3:11])[CH3:10].[Cl:13][CH2:14][C:15](Cl)=[O:16]>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15](=[O:16])[CH2:14][Cl:13])=[C:3]([C:9]([OH:12])([CH3:10])[CH3:11])[CH:4]=1

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 120422752-(2-Amino-5-bromophenyl)propan-2-ol

Product 1

HCID 68864694N-[4-Bromo-2-(1-hydroxy-1-methyl-ethyl)-phenyl]-2-chloro-acetamide

Procedure

Prepared from 2-(2-amino-5-bromophenyl)propan-2-ol and chloro acetyl chloride generally according to the procedure described in example 1. An off-white solid: mp 133-134° C. 1H-NMR (DMSO-d6) δ 11.21 (s, 1H), 8.12 (d, J=8.6 Hz, 1H), 7.46 (dd, J=8.6, 2.3 Hz, 1H), 7.44 (d, J=2.3 Hz, 1H), 6.28 (s, 1H), 4.43 (s, 2H), 1.53 (s, 6H).

Sources & evidence

ORD record: ord-1c00fd48005142318f15caba8be7b47a
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598237B2

Reaction notes

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