تفاعل #77283

معادلة التفاعل

3-[3-(dibromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

dichloromethane

dimethoxymethane

→

title compound

المردود 17.5%

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

المردود 17.5%

المذيبات

ethylene glycol

ethylene glycol

ethylene glycol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred another day at room temperature
2. 2
   workup.STIRRINGAfter stirring an additional day the mixture
3. 3
   ترشيحis filtered
4. 4
   workup.ADDITIONThe filtrate is diluted with dichloromethane
5. 5
   غسيلwashed with water
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe residue is triturated with hexanes-ethyl acetate

الإجراء التجريبي

A mixture of 3-[3-(dibromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.500 g, 10.0 mmol), silver trifluoromethanesulfonate (0.500 g, 19.5 mmol), ethylene glycol (5.00 ml), dichloromethane and dimethoxymethane is stirred three days at room temperature and treated with additional silver trifluoromethanesulfonate (0.300 g, 11.7 mmol). The resultant mixture is stirred one day at room temperature and treated with additional silver trifluoromethanesulfonate (0.400 g, 15.6 mmol) and ethylene glycol (1.00 ml), stirred another day at room temperature and treated again with silver trifluoromethanesulfonate (0.300 g, 11.7 mmol) and ethylene glycol (1.0 ml). After stirring an additional day the mixture is filtered. The filtrate is diluted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is triturated with hexanes-ethyl acetate to afford the title compound as a white solid (0.070 g, 17.5%, mp 213-216° C.) which is identified by NMR spectral analysis.

المصدر