Dimethylformamide dimethyl acetal → HCID 86657917, compound

HRID 2359022Notes

Reaction equation

HRID 2359022 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:16])[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([Cl:15])[CH:10]=2)=[CH:4][CH:3]=1.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>CN(C)C=O>[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:16])[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([Cl:15])[CH:10]=2)=[CH:19][N:20]([CH3:22])[CH3:21])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 86657914HCID 86657914, compound

Product 1

HCID 86657917HCID 86657917, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-(5-chloro-2-thienyl)-2-(2-chloropyridin-4-yl)ethanone (15.8 mmol) in 10 mL N,N-dimethylformamide, was added N,N-dimethylformamide dimethyl acetal (53.7 mmol). The mixture was refluxed for 2 h and then allowed to cool to room temperature. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried over MgSO4 filtered and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate:heptane 6:4 to 1:0) to afford 3.3 g (60% yield) of 1-(5-chloro-2-thienyl)-3-(dimethylamino)-2-(2-chloropyridin-4-yl)prop-2-en-1-one.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (ethyl acetate:heptane 6:4 to 1:0)

Sources & evidence

ORD record
ord-a66eda9aa4ed4c379e80291c50864322
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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