Dimethylformamide → 1-(N,N-dimethylamino)-1-(4-fluorophenyl)-2-(4-methylthiophenyl)prop-1-en-3-one

HRID 2293464Notes

Reaction equation

HRID 2293464 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CO[CH:21](OC)[N:22](C)[CH3:23].CN(C)[CH:29]=[O:30]>>[CH3:21][N:22]([C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[C:9]([C:10]1[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=1)[CH:29]=[O:30])[CH3:23]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 112539741-(4-Fluorophenyl)-2-(4-methylthiophenyl)ethanone

Product 1

HCID 541784881-(N,N-dimethylamino)-1-(4-fluorophenyl)-2-(4-methylthiophenyl)prop-1-en-3-one

Conditions

Temperature
90 °C

Procedure

To a solution of 25.8 g (99.2 mMol) of 1-(4-fluorophenyl)2-(4-methylthiophenyl)ethan-1-one from Step 3 in 200 ml of dimethylformamide was added 33 ml (30 g, 250 mMol) of dimethylformamide dimethyl acetal. The resulting mixture was stirred at 90° C. for 2 hours. Evaporation of the volatiles gave 1-(N,N-dimethylamino)-1-(4-fluorophenyl)-2-(4-methylthiophenyl)prop-1-en-3-one as a yellow solid (32.5 g).

Workup

  1. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-1e273eb14afe490b8e245b7fc5410b7b
Source dataset
uspto-grants-1997_11
Patent number
US05686470

Reaction notes

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