3-Chlorophenylacetic acid → N-(3-chlorophenylacetyl)-2-hydroxy-3-bromo-5-chloroaniline

HRID 842123Notes

Reaction equation

HRID 842123 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[OH:12][C:13]1[C:19]([Br:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:14]=1[NH2:15].C(N1C=CN=C1)(N1C=CN=C1)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:15][C:14]2[CH:16]=[C:17]([Cl:21])[CH:18]=[C:19]([Br:20])[C:13]=2[OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 158793-Chlorophenylacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 155210892-Amino-6-bromo-4-chlorophenol

Product 1

HCID 22618247N-(3-chlorophenylacetyl)-2-hydroxy-3-bromo-5-chloroanilineYield 67.5%

Procedure

Using the normal amide forming conditions, the condensation of 3-chlorophenylacetic acid (13.54 g, 0.079 mol) and 2-hydroxy-3-bromo-5-chloroaniline (17.7 g, 0.079 mol) with 1,1′-carbonyl diimidazole (13.5 g, 0.083 mol) gave the title compound (20 g).

Sources & evidence

ORD record
ord-8cb384c7dedf4082999b9fd54f8ca7c8
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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