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Water → N-(2-Benzoylphenyl)-2-bromoacetamide

HRID 1456633
Notes
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Reaction equation

HRID 1456633 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[NH2:6][C:7]1[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].O>ClCCl>[Br:1][CH2:2][C:3]([NH:6][C:7]1[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 760802-Aminobenzophenone

Product 1

HCID 84439N-(2-Benzoylphenyl)-2-bromoacetamideYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of bromoacetyl bromide (100 mL, 1.15 mol, Aldrich) dissolved in dichloromethane (300 mL) was added over 30 min to a solution of 2-aminobenzophenone (197 g, 1.0 mol, Fluka) dissolved in dichloromethane (1.3 L) and water (100) mL) cooled to -10° C. under vigorous mechanical stirring. The resulting mixture was stirred for an additional 1 h at --5° C. and then was allowed to warm to ambient temperature. The layers were separated, and the organic extract was washed with dilute sodium bicarbonate, then was dried over sodium sulfate. Evaporation afforded 309.8 g (95%) of 2-bromoacetamidobenzophenone as off-white crystals.

Workup

  1. temperatureto warm to ambient temperature
  2. customThe layers were separated
  3. extractionthe organic extract
  4. washwas washed with dilute sodium bicarbonate
  5. dry with materialwas dried over sodium sulfate
  6. customEvaporation

Sources & evidence

ORD record
ord-e71c6b111918467d8dba1546a08d3400
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05843941

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes