Dimethylformamide dimethyl acetal → n-[2-Chloro-5-(3-dimethylamino-acryloyl)-phenyl]-acetamide

HRID 40708Notes

Reaction equation

HRID 40708 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:14])=[C:8]([NH:10][C:11](=[O:13])[CH3:12])[CH:9]=1)(=[O:3])[CH3:2].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[Cl:14][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH:2]=[CH:17][N:18]([CH3:20])[CH3:19])=[CH:9][C:8]=1[NH:10][C:11](=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 18094815'-Acetyl-2'-chloroacetanilide

Product 1

HCID 68565374n-[2-Chloro-5-(3-dimethylamino-acryloyl)-phenyl]-acetamideYield 80.5%

Procedure

4.46 g (21.1 mmol) of N-(5-acetyl-2-chloro-phenyl)-acetamide were dissolved in 10.4 ml (9.34 g) (78.39 mmol) of N,N-dimethylformamide dimethylacetal and the resultant solution was refluxed for 6.5 hours. The excess of volatile reagent was removed by reduced pressure distillation to yield a crude which was crystallized from ethyl acetate. 4.53 g of N-[2-chloro-5-(3-dimethylamino-acryloyl)-phenyl]-acetamide as a yellowish-white solid were obtained (yield 80.5%).

Workup

  1. customThe excess of volatile reagent was removed by reduced pressure distillation
  2. customto yield a crude which
  3. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-8cc390aa0eea455da7e36d5ebbb4761a
Source dataset
uspto-grants-2013_09
Patent number
US08530482B2

Reaction notes

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