p-Aminoacetophenone → N-(4-acetylphenyl)-4-methoxybenzamide

HRID 1766342Notes

Reaction equation

HRID 1766342 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].[C:11](Cl)(=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>C1COCC1>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 7468p-AminoacetophenoneHCID 7477p-Anisoyl chlorideHCID 8471Triethylamine

Product 1

HCID 721316N-(4-acetylphenyl)-4-methoxybenzamideYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 4-aminoacetophenone (74 mg, 0.55 mmol) in THF (6 mL) with p-anisoyl chloride (90 mg, 0.65 mmol) in presence of triethylamine (90 μL, 0.65 mmol) according to method A gave N-(4-acetyl-phenyl)-4-methoxy-benzamide (110 mg, 0.41 mmol, 75% yield) as a white powder after washing by dichloromethane.

Sources & evidence

ORD record
ord-e5034d538777400d9bc552c64f1e2b3e
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

Loading…