Reaction #2200606

Reaction equation

Thioformamide

ethyl 2-chloroacetoacetate

magnesium carbonate

→

4-methyl-5-(ethoxycarbonyl)thiazole

Solvents

dioxane

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to room temperature
2. 2
   Filtrationfiltered
3. 3
   Otherto remove magnesium carbonate
4. 4
   OtherThe solvent was evaporated to dryness
5. 5
   Washwashed successively with 0.5 M NaOH solution (200 mL×2) and saturated brine solution (100 mL)
6. 6
   Dryingdried over Na2SO4
7. 7
   FiltrationIt was filtered
8. 8
   Otherevaporated

Procedure

Thioformamide (7.5 g, 122.72 mmol), ethyl 2-chloroacetoacetate (16.4 g, 99.52 mmol) and magnesium carbonate (20 g, 237.22 mmoL) were taken dioxane (100 mL) and heated at 110° C. for 4 hrs. The reaction mixture was cooled to room temperature and filtered to remove magnesium carbonate. The solvent was evaporated to dryness and the residue was taken in ether (200 mL) and washed successively with 0.5 M NaOH solution (200 mL×2) and saturated brine solution (100 mL) and dried over Na2SO4. It was filtered and evaporated to give 4-methyl-5-(ethoxycarbonyl)thiazole as an oil which was purified by silica gel column chromatography using hexanes:EtOAc (8:2, v/v) as a eluent; yield: 3.28 g (17%).

Source