Dimethylformamide dimethyl acetal → 1-(3-trifluoromethylbenzoyl)-1-methanesulfonyl-2-(N,N-dimethylamino)ethene

HRID 2226704Notes

Reaction equation

HRID 2226704 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9](=[O:15])[CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>C1(C)C=CC=CC=1>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[C:9]([C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:20][N:21]([CH3:23])[CH3:22])=[O:15]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 27755062-(Methylsulfonyl)-1-(3-(trifluoromethyl)phenyl)ethanone

Product 1

HCID 541640061-(3-trifluoromethylbenzoyl)-1-methanesulfonyl-2-(N,N-dimethylamino)etheneYield 99.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.5 g of m-trifluoromethyl-α-methanesulfonylacetophenone and 1.4 g of N,N-dimethylformamide dimethylacetal were dissolved in 40 ml of toluene, and the resulting mixture was heated under reflux for 2 hours. The solvent was distilled away under reduced pressure. The residue was treated with column chromatography on silica gel, thereby obtaining 3 g of 1-(3-trifluoromethylbenzoyl)-l-methanesulfonyl-2-(N,N-dimethylamino)ethene (Compound 205).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationThe solvent was distilled away under reduced pressure
  4. additionThe residue was treated with column chromatography on silica gel

Sources & evidence

ORD record
ord-16f91b131a9540208f478a2cd7fa2a70
Source dataset
uspto-grants-1994_09
Patent number
US05349108

Reaction notes

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