Dimethylformamide dimethyl acetal → 1-(4-Chloro-2-thienyl)-3-(dimethylamino)prop-2-en-1-one

HRID 2359058Notes

Reaction equation

HRID 2359058 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7](=[O:9])[CH3:8])[S:5][CH:6]=1.CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:7](=[O:9])[CH:8]=[CH:12][N:13]([CH3:15])[CH3:14])[S:5][CH:6]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 111056552-Acetyl-4-chlorothiophene

Product 1

HCID 672602831-(4-Chloro-2-thienyl)-3-(dimethylamino)prop-2-en-1-oneYield 77%

Procedure

A mixture of 1-(4-chloro-2-thienyl)ethanone (32.1 mmol) and N,N-dimethylformamide dimethyl acetal (112.2 mmol) was refluxed for 3 h and then allowed to cool to room temperature whereupon crystallization occurred. The reaction mixture was stored in a freezer at −18° C. for 2 h. The supernatant liquid was decanted, the crystals were dried in vacuum to afford 5.3 g (77% yield) of 1-(4-chloro-2-thienyl)-3-(dimethylamino)prop-2-en-1-one which was used in the next step without further purification.

Workup

  1. temperaturewas refluxed for 3 h
  2. customThe supernatant liquid was decanted
  3. customthe crystals were dried in vacuum

Sources & evidence

ORD record
ord-30d50fe51cae4e57a0628dfa6b953a24
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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