Dimethylformamide dimethyl acetal → 3-(Dimethylamino)-2-phenyl-1-(thiophen-2-yl)prop-2-en-1-one

HRID 2267439Notes

Reaction equation

HRID 2267439 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[CH3:17][N:18]([CH3:20])[CH:19]=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)=[O:9]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 6870902-Phenyl-1-(2-thienyl)ethanone

Product 1

HCID 684631243-(Dimethylamino)-2-phenyl-1-(thiophen-2-yl)prop-2-en-1-one

Conditions

Temperature
100 °C

Procedure

2-Phenyl-1-(thiophen-2-yl)ethanone (1 g, 4.94 mmol) was treated with dimethylformamide dimethylacetal (5 mL) and heated to 100° C. while stirring. After 4 h, the reaction was allowed to cool down to room temperature. The solid that precipitated out of the reaction mixture was collected by filtration and washed with a 1:1 mixture of diethyl ether and hexanes to afford a yellow crystalline solid (1 g). MS (M+H)+ 258.

Workup

  1. temperatureto cool down to room temperature
  2. customThe solid that precipitated out of the reaction mixture
  3. filtrationwas collected by filtration
  4. washwashed with a 1:1 mixture of diethyl ether and hexanes

Sources & evidence

ORD record
ord-4fe77954bec84835be4c45c5608f842b
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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