Triethylamine → 4-bromo-N,N-dimethylbenzamide

HRID 1604604Notes

Reaction equation

HRID 1604604 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C(N(CC)CC)C.[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>ClCCl>[CH3:2][N:3]([CH3:4])[C:17]([C:16]1[CH:20]=[CH:21][C:13]([Br:12])=[CH:14][CH:15]=1)=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 685154-Bromobenzoyl chloride

Product 1

HCID 1403894-bromo-N,N-dimethylbenzamideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of dimethylamine hydrochloride (2.79 g) and triethylamine (6.92 g) in dichloromethane (50 ml) was added 4-bromobenzoyl chloride (5 g) was added slowly under ice-cooling, and the mixture was stirred for 20 minutes at the same temperature and for 2 hours at ambient temperature. The mixture was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated invacuo to give 4-(dimethylcarbamoyl)-1-bromobenzene (5.20 g) as brown oil.

Workup

  1. additionwas added slowly under ice-
  2. temperaturecooling
  3. washThe mixture was washed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated invacuo

Sources & evidence

ORD record
ord-9d5e8d02d69c4155b9021ab75f563f03
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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