Réaction #4496

Équation de réaction

cyclohexanethiocarboxamide

ethyl 4-chloroacetoacetate

→

ethyl 2-cyclohexyl-4-thiazoleacetate

Rendement 71.3%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureunder reflux for 1 hour
3. 3
   ExtractionAfter dilution with water, mixture was extracted with ethyl acetate
4. 4
   LavageThe extract was washed with aqueous sodium bicarbonate solution and water
5. 5
   Séchagedried (MgSO4)
6. 6
   Concentrationconcentrated
7. 7
   AutreThe residue was purified by chromatography on silica gel with ethyl acetate-hexane (1:4)

Mode opératoire

A mixture of cyclohexanethiocarboxamide (5.0 g), ethyl 4-chloroacetoacetate (5.74 g), ethanol (50 ml) was heated under reflux for 1 hour. After dilution with water, mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium bicarbonate solution and water, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel with ethyl acetate-hexane (1:4) to yield ethyl 2-cyclohexyl-4-thiazoleacetate as an oil (6.3 g, 70.9%). IR (Neat): 1735, 1255 cm-1. NMR (CDCl3)δ: 1.28 (3H, t, J=7 Hz), 1.2-2.3 (10H, m), 2.97 (1H, m), 3.77 (2H, s), 4.17 (2H, q, J=7 Hz), 7.0 (1H, s).

Source