Réaction #77291

Équation de réaction

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

2-aminoethanethiol

triethylamine

acetyl chloride

→

title compound

Rendement 93.3%

3-Acetyl-2-[5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl]thiazolidine

Rendement 93.3%

Solvants

tetrahydrofuran

ethanol

water

Conditions de réaction

Traitement

1. 1
   ConcentrationThe mixture is concentrated in vacuo
2. 2
   LavageThe organic layer is washed with brine
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated in vacuo to a white solid, which
5. 5
   Autreis chromatographed on silica gel with methanol-methylene chloride

Mode opératoire

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), 2-aminoethanethiol (0.13 g, 1.69 mmol), ethanol and tetrahydrofuran is stirred overnight at room temperature. The mixture is concentrated in vacuo and the residue taken up in methylene chloride. The resultant mixture is treated with triethylamine (0.340 ml, 2.41 mmol), then acetyl chloride (0.120 ml, 1.69 mmol), stirred 90 minutes and poured into water. The resultant mixture is diluted with methylene chloide. The organic layer is washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to a white solid, which is chromatographed on silica gel with methanol-methylene chloride to afford the title compound as a white solid (0.600 g, 93.3%, mp 135-140° C.) which is identified by NMR spectral analysis.

Source