Reaction #60640

Reaction equation

1-(4-methyl-2-methylamino-thiazol-5-yl)-ethanone

NaH

MeI

→

1-(2-dimethylamino-4-methyl-thiazol-5-yl)-ethanone

Solvents

THF

EtOAc

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureHeating
3. 3
   TemperatureAfter cooling
4. 4
   Washwashed with brine
5. 5
   Dryingdried over MgSO4
6. 6
   OtherThe solvent was evaporated

Procedure

A mixture of 1-(4-methyl-2-methylamino-thiazol-5-yl)-ethanone (0.40 g, 2.4 mmol) in THF (2 mL) was treated with NaH (0.113 g, 4.7 mmol). After heating at 40° C. for 0.5 h MeI (0.35 g, 2.4 mmol) was added. Heating was continued for a further 2 h. After cooling, the solution was diluted with EtOAc, washed with brine, and dried over MgSO4. The solvent was evaporated to afford 1-(2-dimethylamino-4-methyl-thiazol-5-yl)-ethanone as a yellow solid. 1H-NMR (CDCl3) δ: 2.36 (s, 3H, CH3), 2.51 (s, 3H, CH3), 3.10 (s, 6H, CH3).

Source