Triethylamine → 4-bromo-N-methoxy-N,3-dimethylbenzamide

HRID 1776024Notes

Reaction equation

HRID 1776024 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[CH3:11].[CH3:12][O:13][NH:14][CH3:15].C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:14]([O:13][CH3:12])[CH3:15])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 821314-Bromo-3-methylbenzoic acid

Product 1

HCID 218337954-bromo-N-methoxy-N,3-dimethylbenzamideYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromo-3-methyl-benzoic acid (15 g, 0.069 mol), O,N-dimethyl hydroxylamine (6.5 g, 0.1 mol) HATU (38 g, 0.1 mol), and triethylamine (20 g, 0.2 mol) dissolved in DMF (50 mL) was stirred at RT for 12 h, concentrated, and purified by silica gel chromatography (1:1 EtOAc:petroleum ether) to provide the title intermediate (11 g, 61% yield) 1H NMR (CDCl3, 400 MHz) δ (ppm): 7.52 (m, 2H), 7.32 (m, 1H), 3.50 (s, 3H), 3.29 (m, 3H), 2.38 (s, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography (1:1 EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-9192d85ab47146b3953a5d880fe20ff5
Source dataset
uspto-grants-2016_02
Patent number
US09260414B2

Reaction notes

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