4-Bromobenzoyl chloride → 4-bromo-N-(2,2-dimethoxyethyl)benzamide

HRID 2251194Notes

Reaction equation

HRID 2251194 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].C(=O)([O-])O.[K+].[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>O.CC(C)=O>[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 516893Potassium Bicarbonate

Product 1

HCID 111299414-bromo-N-(2,2-dimethoxyethyl)benzamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 24 mmol aminoacetaldehyde dimethylacetal was dissolved in 30 ml of water and treated with 25 mmol of potassium hydrogencarbonate. A solution of 23 mmol of 4-bromobenzoyl chloride in 50 ml of acetone was slowly added under stirring over a period of 30 min. The acetone was evaporated and the aqueous phase was extracted 3 times with ethyl acetate to yield the crude title compound as a slightly brown solid.

Workup

  1. customThe acetone was evaporated
  2. extractionthe aqueous phase was extracted 3 times with ethyl acetate

Sources & evidence

ORD record
ord-763d1e0b34db4b7c9cb11fc37f20917b
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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