Dimethylamine → 4-(bromomethyl)-N,N-dimethylbenzamide

HRID 1634021Notes

Reaction equation

HRID 1634021 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[N:12]1[CH:17]=CC=C[CH:13]=1.CNC>>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:12]([CH3:17])[CH3:13])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 1049PyridineHCID 50682894-Bromomethyl-benzoyl chloride

Product 1

HCID 186770234-(bromomethyl)-N,N-dimethylbenzamideYield 99.7%

Conditions

Temperature
23 °C

Procedure

A mixture of 4-bromomethyl-benzoyl chloride (7.0 g, 30.24 mmol), polyvinyl pyridine (9.6 g, 90.7 mmol) and dimethyl amine (15.9 ml, 31.8 mmol, 2.0 M in THF) was stirred at 23° C. for 15 h. The solution was filtered and the solvent removed to give 7.3 g (99% yield) of 4-bromomethyl-N,N-dimethyl-benzamide as a yellow solid.

Workup

  1. filtrationThe solution was filtered
  2. customthe solvent removed

Sources & evidence

ORD record
ord-b0a94fe1c5d54929915b223100cce8e7
Source dataset
uspto-grants-2003_01
Patent number
US06506738B1

Reaction notes

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