Acetamide, 2-cyano-N-phenyl- → 2-Propenamide, 2-cyano-3-(dimethylamino)-N-phenyl-, (Z)-

HRID 1074593Notes

Reaction equation

HRID 1074593 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])#[N:2].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>>[C:1]([C:3](=[CH:15][N:16]([CH3:18])[CH3:17])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])#[N:2]

Participants

3

Reactant 2

HCID 69296Acetamide, 2-cyano-N-phenyl-HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 45854682-Propenamide, 2-cyano-3-(dimethylamino)-N-phenyl-, (Z)-

Procedure

A 10.0 g. amount of 2-cyanoacetanilide in 25 ml. of N,N-dimethylformamide dimethylacetal is heated on a steam bath for 2-6 hours. The reaction mixture volatiles are removed in vacuo and the resultant solid is dissolved in dichloromethane. The solution is passed through a short column of hydrous magnesium silicate, then n-hexane is added to the effluent until crystallization is noted. After cooling, the product is collected by filtration to give 2-cyano-3-dimethylamino-acrylanilide as colorless plates, m.p. 162.5°-164° C.

Workup

  1. customThe reaction mixture volatiles are removed in vacuo
  2. dissolutionthe resultant solid is dissolved in dichloromethane
  3. additionn-hexane is added to the
  4. customeffluent until crystallization
  5. temperatureAfter cooling
  6. filtrationthe product is collected by filtration

Sources & evidence

ORD record
ord-179bca92898d4f9a9307caa922cdc874
Source dataset
uspto-grants-1983_07
Patent number
US04393217

Reaction notes

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