Benzoyl chloride → N,N-Diethylbenzamide

HRID 1089188Notes

Reaction equation

HRID 1089188 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:1]([N:3]([CH2:4][CH3:5])[C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8021DiethylamineHCID 8471Triethylamine

Product 1

HCID 15542N,N-DiethylbenzamideYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2.5 g of diethylamine and 3.5 g of triethylamine in 30 ml of methylene chloride was cooled in an ice bath while 4.9 g of benzoyl chloride was added dropwise. The cooling bath was removed and the mixture stirred at ambient temperature for 18 hours. The insolubles were removed by filtration followed by methylene chloride washing. The combined filtrates were washed with water and brine, dried and evaporated to a yellow oil which was distilled in a Kugelrohr still to give 5.91 g of the desired product as a colorless oil, 70°/300 mm.

Workup

  1. additionwas added dropwise
  2. customThe cooling bath was removed
  3. customThe insolubles were removed by filtration
  4. washThe combined filtrates were washed with water and brine
  5. customdried
  6. customevaporated to a yellow oil which
  7. distillationwas distilled in a Kugelrohr still

Sources & evidence

ORD record
ord-3db607a9b93f41d69a8ab3ba4b0b4cb0
Source dataset
uspto-grants-1990_10
Patent number
US04965284

Reaction notes

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