Bromoacetyl bromide → N-(2-Benzoylphenyl)-2-bromoacetamide

HRID 1085430Notes

Reaction equation

HRID 1085430 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[Br:16][CH2:17][C:18](Br)=[O:19]>ClCCl.O>[Br:16][CH2:17][C:18]([NH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])=[O:19]

Participants

5

Reactant 2

HCID 61147Bromoacetyl bromideHCID 760802-Aminobenzophenone

Product 1

HCID 84439N-(2-Benzoylphenyl)-2-bromoacetamideYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

98.6 g of 2-aminobenzophenone were dissolved in a mixture of 650 ml of dichloromethane and 50 ml of water. A solution of 116.1 g of bromoacetyl bromide in 150 ml of dichloromethane was added dropwise to this mixture at a temperature of -10° C. The reaction mixture was then stirred at room temperature for a further 2 hours. The reaction mixture was worked up by adding water, separating the organic phase, washing again with water, drying and evaporating under reduced pressure. The crude product remaining as a residue was crystallized from ether/petroleum ether. 142 g of 2-[(2-bromoacetyl)-amino]-benzophenone having a melting point of 96-98° C. were obtained.

Workup

  1. customseparating the organic phase
  2. washwashing again with water
  3. customdrying
  4. customevaporating under reduced pressure
  5. customwas crystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-6e10960923f048ef807964b6de8cd466
Source dataset
uspto-grants-1991_04
Patent number
US05010076

Reaction notes

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