Reaktion #77291

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 93.3%

Lösungsmittel

tetrahydrofuran

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture is concentrated in vacuo
2. 2
   WaschenThe organic layer is washed with brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated in vacuo to a white solid, which
5. 5
   Sonstigeis chromatographed on silica gel with methanol-methylene chloride

Vorschrift

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.

Quelle