Reaction #75475

Reaction equation

5-acetyl-2,4-dimethylthiazole

N,N-dimethylformamide dimethylacetal

→

title compound

Yield 79.0%

3-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone

Yield 79.0%

Conditions

Workup

1. 1
   Otherthe reaction mixture was evaporated to dryness
2. 2
   Otherthe residue was recrystallised from iPr2O/CH2Cl2

Procedure

A solution of 5-acetyl-2,4-dimethylthiazole (10 g, 60 mmol) in N,N-dimethylformamide dimethylacetal (10 mL) was refluxed under N2. After 18 h, the reaction mixture was evaporated to dryness and the residue was recrystallised from iPr2O/CH2Cl2 to afford the title compound as a brown powder (9.94 g, 79%). 1H-NMR (300 MHz, CDCl3) δ2.66 (s, 6H, CH3), 2.70 (s, 6H, CH3), 5.37 (d, 1H, J=12.2 Hz, CH), 7.66 (d, 1H, J=12.2 Hz, CH).

Source