Aniline → 3-Amino-4-chloro-N-phenylbenzamide

HRID 1859655Notes

Reaction equation

HRID 1859655 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=1[N+:17]([O-])=O.CN(C=O)C.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CCCCCC>[NH2:17][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:8]=1[Cl:7])[C:12]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:14]

Participants

6

Reactant 4

HCID 6115AnilineHCID 6228DimethylformamideHCID 73204-Chloro-3-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 167780693-Amino-4-chloro-N-phenylbenzamideYield 68.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Prepared according to the procedure described for Example 1 using oxalyl chloride (2.5 mL, 28.66 mmol), 4-chloro-3-nitrobenzoic acid (4.02 g, 19.94 mmol), DMF (1.0 mL, 12.92 mmol), and aniline (3.6 mL, 39.51 mmol) to afford the product (3.39 g) after trituration in hexane; m.p. 194-197° C. after recrystallization from ethyl acetate.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-df62c0bcfd924ac7b7866454c620e228
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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