Pyridine → 4-(acetylamino)-N-(2,6-dimethylphenyl)benzamide

HRID 236064

Reaction equation

HRID 236064 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25](Cl)(=[O:27])[CH3:26]>CN(C)C=O.O>[C:25]([NH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[O:7])=[CH:4][CH:3]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 13086Ameltolide

Product 1

HCID 4432274-(acetylamino)-N-(2,6-dimethylphenyl)benzamideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 2.0 g of 4-amino-N-(2,6-dimethylphenyl)benzamide in dimethylformamide were added 1 ml of pyridine followed by 710 μl of acetyl chloride. The reaction was stirrred at room temperature for 2 hours, diluted with water, and chilled to approximately 4° C. The title product was recovered by filtration in 85% yield, m.p. 293°-295° C.

Workup

  1. filtrationThe title product was recovered by filtration in 85% yield, m.p. 293°-295° C.

Sources & evidence

ORD record
ord-0da184272f6b474bb5fac4687f8f7171
Source dataset
uspto-grants-1987_02
Patent number
US04642379

Linked notes

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