Dimethylformamide dimethyl acetal → 3-(Dimethylamino)-2-(4-fluorophenyl)-1-[4-(methylthio)phenyl]prop-2-en-1-one

HRID 1080490Notes

Reaction equation

HRID 1080490 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>CN(C=O)C.C(OCC)(=O)C>[CH3:21][N:22]([CH3:24])[CH:23]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 114709614-Fluorophenyl-1-[4-(methylthio)phenyl]ethanone

Product 1

HCID 701881703-(Dimethylamino)-2-(4-fluorophenyl)-1-[4-(methylthio)phenyl]prop-2-en-1-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Fluorophenyl)-1-[4-(methylthio)phenyl]ethanone from Example 1, Step 1 (17.2 g, 66 mmol) was stirred with 15 mL dimethylformamide dimethylacetal in 80 mL dry DMF at 120° C. for 24 hours under nitrogen. The reaction mixture was cooled, diluted with two volumes of ethyl acetate, and the solution washed successively with water and brine and dried over Na2SO4. The solvent was removed under high vacuum and the resulting brown oil (23.9 g) was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washthe solution washed successively with water and brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under high vacuum
  5. customthe resulting brown oil (23.9 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-1b804a41d6ec41b583b0be639b9082cb
Source dataset
uspto-grants-1996_12
Patent number
US05580985

Reaction notes

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