Reaction #2200607

Reaction equation

4-methyl-5-(hydroxymethyl)thiazole

2-chloroacetophenone

Acetonitrile

→

3-(2-Phenyl-2-oxoethyl)-4-methyl-5-(hydroxymethyl)thiazolium chloride

Solvents

tert-butyl methyl ether

Conditions

Workup

1. 1
   Temperaturethe mixture refluxed for another 3 hrs
2. 2
   TemperatureIt was cooled to room temperature
3. 3
   workup.WAITthe reaction mixture was left overnight at room temperature
4. 4
   OtherThe product crystallized
5. 5
   Filtrationwas filtered
6. 6
   Washwashed well with a mixture of hexanes: EtOAc (1:1
7. 7
   Otherv/v) and dried
8. 8
   OtherIt was recrystallized from a mixture of acetonitrile/ethanol/ tert-butyl methyl ether

Procedure

The neat reaction of 4-methyl-5-(hydroxymethyl)thiazole (590 mg, 4.57 mmol) and 2-chloroacetophenone (710 mg, 4.59 mmol) was heated at 110° C. The mixture solidified within 15 minutes. Acetonitrile (10 mL) was added and the mixture refluxed for another 3 hrs. It was cooled to room temperature and tert-butyl methyl ether (5 mL) was added and the reaction mixture was left overnight at room temperature. The product crystallized was filtered and washed well with a mixture of hexanes: EtOAc (1:1, v/v) and dried. It was recrystallized from a mixture of acetonitrile/ethanol/ tert-butyl methyl ether; yield 130 mg (10%); mp.240-242° C. (dec.).

Source