Dimethylformamide dimethyl acetal → HCID 66991250, compound

HRID 40706Notes

Reaction equation

HRID 40706 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([F: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]>>[CH3:17][N:18]([CH3:20])[CH:19]=[CH:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([F:14])=[C:8]([NH:10][C:11](=[O:13])[CH3:12])[CH:9]=1)=[O:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 53431926N-(5-Acetyl-2-fluorophenyl)acetamide

Product 1

HCID 66991250HCID 66991250, compoundYield 78.6%

Procedure

3.3 g (16.9 mmol) of N-(5-acetyl-2-fluoro-phenyl)-acetamide were dissolved in 8.36 ml (7.49 g) (62.89 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. 3.32 g of N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyl]-acetamide as a yellowish-white solid were obtained (yield 78.6%).

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-a5042f2a4eaa4ef7b250a3014ed2d524
Source dataset
uspto-grants-2013_09
Patent number
US08530482B2

Reaction notes

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