Water → 3-Bromo-N-methoxy-N-methylbenzamide

HRID 496652Notes

Reaction equation

HRID 496652 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].Cl.[CH3:12][NH:13][O:14][CH3:15].C(N(CC)CC)C.O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([N:13]([O:14][CH3:15])[CH3:12])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 74377Benzoyl chloride, 3-bromo-HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 121628753-Bromo-N-methoxy-N-methylbenzamideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100.0 g (0.447 mol) 3-bromobenzoyl chloride was added to an ice cooled solution of 48.9 g (0.491 mol) N,O-dimethylhydroxylamine hydrochloride and 140.0 ml (1.00 mol) triethylamine in 650 ml dry dichloromethane over a period of 30 minutes. After additional stirring for 30 minutes, 370 ml water was added and the organic layer dried over sodium sulfate. Fractionated distillation in vacuo yielded 101.4 g (93%) B1, b.p. 114-129° C./0.07 mbar, as a colorless oil.

Workup

  1. dry with materialthe organic layer dried over sodium sulfate
  2. distillationFractionated distillation in vacuo

Sources & evidence

ORD record
ord-be13bd604fcd4daab0395d276c40f343
Source dataset
uspto-grants-2005_09
Patent number
US06946471B2

Reaction notes

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