تفاعل #319158

معادلة التفاعل

sulfonamide

2-[[5-(Methylthio)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamide

phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate

1.8-diazabicyclo[5.4.0]undec-7-ene

→

subject compound

المردود 19.8%

N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamide

المردود 19.8%

المذيبات

p-dioxane

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصAfter extracting the cloudy aqueous solution 1×30 ml of diethyl ether
2. 2
   ترشيحthe suspension was filtered
3. 3
   أخرىThe residue was triturated with 5 ml of warm ethyl acetate

الإجراء التجريبي

To a suspension containing 0.63 g of the sulfonamide prepared in Example 3 in 10 ml of p-dioxane was added 0.6 g phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate followed by dropwise addition of 0.33 g of 1.8-diazabicyclo[5.4.0]undec-7-ene (DBU). The solution was stirred at room temperature for two hours then diluted with about 75 ml of water. After extracting the cloudy aqueous solution 1×30 ml of diethyl ether, the clear aqueous layer was acidified with concentrated hydrochloric acid (red to litmus paper), and the suspension was filtered. The residue was triturated with 5 ml of warm ethyl acetate to give 0.2 g of the subject compound; m.p. 171°-175° C. NMR (CDCl3, DMSO-d6): δ 2.7(s, SCH3); 4.0(s, OCH3); 4.95(s, CH2); 5.9(s, pyrimidine H); 7.6-8.4(m, ar); 9.8(s, NH) ppm.

المصدر