Dimethylformamide dimethyl acetal → N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamide

HRID 2184796Notes

Reaction equation

HRID 2184796 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([CH3:13])=[O:12])[CH:5]=1)=[O:3].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[CH3:16][N:17]([CH3:19])[CH:18]=[CH:1][C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:12])[CH3:13])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 3462023'-Acetamidoacetophenone

Product 1

HCID 53412415N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamideYield 95%

Procedure

A mixture of 3-acetamidoacetophenone (30 g, 169 mmol) and dimethylformamide dimethyl acetal (50 mL, 376 mmol) is refluxed under nitrogen for 8 hours. The reaction mixture is cooled and the solid collected by filtration to yield product (5) as an orange solid (37.2 g, 160 mmol, 95%).

Workup

  1. temperatureis refluxed under nitrogen for 8 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-b47f7c40eef64233a192c59ce323971e
Source dataset
uspto-grants-2002_06
Patent number
US06399621B1

Reaction notes

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