Reacción #77284

Ecuación de reacción

water

5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde

1,2-propanediol

toluene

→

title compound

Rendimiento 87.6%

1-Methyl-3-[3-(4-methyl-1,3-dioxolan-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil

Rendimiento 87.6%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed twice with water and once with brine
2. 2
   Secadodried over anhydrous magnesium sulfate
3. 3
   ConcentraciónConcentration in vacuo
4. 4
   Otroaffords a yellow oil, which
5. 5
   Otrois chromatographed on silica gel

Procedimiento

A mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (0.500 g, 1.41 mmol), 1,2-propanediol (0.130 ml, 1.83 mmol), p-toluenesulfonic acid (0.0100 g, 0.0100 g, 0.071 mmol) and toluene is stirred at reflux with azeotropic removal of water overnight, cooled to room temperature, diluted with diethyl ether, washed twice with water and once with brine and dried over anhydrous magnesium sulfate. Concentration in vacuo affords a yellow oil, which is chromatographed on silica gel to afford the title compound as a yellow solid (0.510 g, 87.6%, mp 81-83° C.) which is identified by NMR spectral analysis.

Fuente