p-Toluidine → N-[4-[(4-methylphenyl)amino]phenyl]acetamide

HRID 1354971Notes

Reaction equation

HRID 1354971 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8](Cl)=[CH:7][CH:6]=1)=[O:3].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.CCCCCC>C(OCC)(=O)C>[C:16]1([CH3:19])[CH:17]=[CH:18][C:13]([NH:12][C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:2](=[O:3])[CH3:1])=[CH:6][CH:7]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 8058HexaneHCID 10871N-(4-Chlorophenyl)acetamide

Product 1

HCID 10586135N-[4-[(4-methylphenyl)amino]phenyl]acetamideYield 98.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the general procedure, 4-chloroacetanilide (85 mg, 0.5 mmol) was coupled with p-toluidine (80 mg, 0.75 mmol) with the reaction temperature of 90° C. and the reaction time of 14 h. Chromatography on silica gel column with 2:1 hexane:ethyl acetate gave 118 mg (98%) of the title compound as a pink solid.

Workup

  1. customthe reaction time of 14 h

Sources & evidence

ORD record
ord-6ed14b918ba94f38a795dc15fddd7e83
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

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