4-Chloroaniline → 2-amino-N-(4-chlorophenyl)benzamide

HRID 644160Notes

Reaction equation

HRID 644160 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>C(Cl)Cl>[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2](=[O:4])[C:1]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH2:6])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 8359Isatoic Anhydride

Product 1

HCID 6704722-amino-N-(4-chlorophenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 20 g (123 mmol) isatoic anhydride (formed by treating anthranilic acid with phosgene) and 15.64 g (123 mmol) 4-chloroaniline was heated at 120° C. for 2 hours. The reaction was cooled to room temperature, mixed with CH2Cl2 and filtered.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-f105896d76a74ce7a459cb137e629911
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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