Sodium Carbonate → 2-Bromo-N-[4-chloro-2-(4-hydroxybenzoyl)phenyl]acetamide

HRID 1701122Notes

Reaction equation

HRID 1701122 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)=[O:5].[Br:18][CH2:19][C:20](Br)=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>CCOCC.O>[Br:18][CH2:19][C:20]([NH:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4](=[O:5])[C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)=[O:21]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 61147Bromoacetyl bromideHCID 11402375Methanone, (2-amino-5-chlorophenyl)(4-hydroxyphenyl)-

Product 1

HCID 125173062-Bromo-N-[4-chloro-2-(4-hydroxybenzoyl)phenyl]acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 41 g (0.165 mole) 2-amino-5-chloro-4'-hydroxybenzophenone in 800 ml of ether and 200 ml of water was cooled to 5°. The mixture was stirred while 20 ml (0.277 mole) of bromoacetyl bromide and a 20% solution of sodium carbonate were added alternately keeping the solution slightly basic. After 20 min. the reaction mixture was filtered to collect 60 g (about 100%) of product mp 201°-202°. Recrystallization from ethanol gave colorless prisms, mp 201°-203°.

Workup

  1. filtrationAfter 20 min. the reaction mixture was filtered
  2. customto collect 60 g (about 100%) of product mp 201°-202°
  3. customRecrystallization from ethanol
  4. customgave colorless prisms, mp 201°-203°

Sources & evidence

ORD record
ord-316fd8d237434beea9e09ac7ad5d18aa
Source dataset
uspto-grants-1980_03
Patent number
US04191738

Reaction notes

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