2-Acetylthiophene → beta-Dimethylamino-1-(2-thienyl)-2-propen-1-one

HRID 2184793Notes

Reaction equation

HRID 2184793 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].CO[CH:11](OC)[N:12](C)[CH3:13].[CH3:17]CCCCC>>[CH3:11][N:12]([CH3:13])[C:2](=[CH2:17])[C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)=[O:3]

Participants

4

Reactant 3

HCID 69202-AcetylthiopheneHCID 8058HexaneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 22288452beta-Dimethylamino-1-(2-thienyl)-2-propen-1-oneYield 63%

Procedure

A mixture of 2-acetylthiophene (10.0 g, 80 mmol) (Aldrich) and dimethylformamide dimethyl acetal (15 g, 126 mmol) is refluxed under nitrogen for 3 hrs, The reaction mixture is cooled and hexane (300 mL) added. The solid is collected by filtration to yield product (1) as an orange solid (9.1 g, 50 mmol, 63%).

Workup

  1. temperatureis refluxed under nitrogen for 3 hrs
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe solid is collected by filtration

Sources & evidence

ORD record
ord-86743a5ccd854d649785bebd26b69f78
Source dataset
uspto-grants-2002_06
Patent number
US06399621B1

Reaction notes

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