반응 #77280

반응 방정식

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

diethyl malonimidate dihydrochloride

diisopropylethylamine

oxalyl chloride

→

title compound

수율 8.3%

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

수율 8.3%

용매

N,N-dimethylformamide

diethyl ether

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   기타the supernatant is decanted
2. 2
   농축concentrated in vacuo
3. 3
   온도to warm to room temperature
4. 4
   세척washed with water, 10% aqueous hydrochloric acid and water
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   농축concentrated in vacuo

실험 절차

To a cooled mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid (3.71 g, 10.0 mmol), diethyl ether and N,N-dimethylformamide (3.0 ml) is added oxalyl chloride (1.52 g, 12.0 mmol). The mixture is allowed to warm to room temperature and stirred overnight. The mixture is allowed to settle and the supernatant is decanted and concentrated in vacuo. The residue is taken up in methylene chloride and added dropwise to a stirred mixture of diethyl malonimidate dihydrochloride (2.31 g, 10.0 mmol), diisopropylethylamine (10 ml) and methylene chloride at −40° C. over one hour. The resultant mixture is allowed to warm to room temperature, diluted with methylene chloride, washed with water, 10% aqueous hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford the title compound as a white solid (0.410 g, 8.31%, mp 197-200° C.) which is identified by NMR spectral analysis.

출처