تفاعل #77292

معادلة التفاعل

3-mercapto-1-propanol

bismuth (III) chloride

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

3-mercapto-1-propanol

bismuth (III) chloride

acetonitrile

→

title compound

المردود 39.2%

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

المردود 39.2%

المذيبات

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   تركيزthe resultant mixture is concentrated in vacuo
2. 2
   أخرىThe residue is chromatographed with ethyl acetate-hexanes
3. 3
   أخرىto afford a solid, which
4. 4
   غسيلwashed with water, once with brine
5. 5
   تجفيفdried over anhydrous magnesium sulfate
6. 6
   تركيزConcentration in vacuo

الإجراء التجريبي

A mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (2.86 g, 8.05 mmol), 3-mercapto-1-propanol (0.600 ml, 6.84 mmol), bismuth (III) chloride (0.090 g, 0.285 mol) and acetonitrile is stirred overnight at room temperature. Additional 3-mercapto-1-propanol (0.200 ml, 2.31 mmol) and bismuth (III) chloride are added and the resultant mixture is concentrated in vacuo. The residue is chromatographed with ethyl acetate-hexanes to afford a solid, which is taken up in diethyl ether, washed with water, once with brine and dried over anhydrous magnesium sulfate. Concentration in vacuo affords the title compound as a white solid (1.15 g, 33.2%, mp 125-130° C.) which is identified by NMR spectral analysis.

المصدر