反応 #586111

反応方程式

(2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimdin-1-yl)-4-fluorobenzoyloxy]-2-methylpropionic acid

N,N-dimethylsulfamide

triethylamine

→

title compound

2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-di-hydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]-2-methylpropionic acid N,N-dimethylsulfamide

溶媒

thionyl chloride

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   温度the reaction mixture was heated
2. 2
   温度under reflux for 3 hours
3. 3
   濃縮the resulting solution of the acid chloride was then concentrated
4. 4
   workup.ADDITIONwas then added dropwise
5. 5
   濃縮concentrated
6. 6
   workup.DISSOLUTIONthe residue was then dissolved in ethyl acetate
7. 7
   洗浄The organic phase was washed with 10% strength hydrochloric acid and water
8. 8
   乾燥the organic phase was dried over sodium sulfate
9. 9
   ろ過the drying agent was filtered off
10. 10
    濃縮the filtrate was concentrated

実験手順

0.65 g (1.4 mmol) of 2-[(2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimdin-1-yl)-4-fluorobenzoyloxy]-2-methylpropionic acid from example 4.2 was dissolved in 30 ml of thionyl chloride, the reaction mixture was heated under reflux for 3 hours and the resulting solution of the acid chloride was then concentrated. 0.18 g (1.4 mmol) of N,N-dimethylsulfamide, 0.07 g (1.4 mmol) of 4-dimethylaminopyridine and 0.35 ml (3.5 mmol) of triethylamine were dissolved in 10 ml of dichloromethane, and a solution of the acid chloride which had been prepared beforehand in 10 ml of dichloromethane was then added dropwise. The solution was stirred for 16 hours and then concentrated, and the residue was then dissolved in ethyl acetate. The organic phase was washed with 10% strength hydrochloric acid and water, the organic phase was dried over sodium sulfate, the drying agent was filtered off and the filtrate was concentrated. Column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1) gave 0.30 g of the title compound of melting point 211-213° C.

出典