반응 #586111

반응 방정식

(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

용매

thionyl chloride

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   온도under reflux for 3 hours
3. 3
   농축the resulting solution of the acid chloride was then concentrated
4. 4
   workup.ADDITIONwas then added dropwise
5. 5
   농축concentrated
6. 6
   workup.DISSOLUTIONthe residue was then dissolved in ethyl acetate
7. 7
   세척The organic phase was washed with 10% strength hydrochloric acid and water
8. 8
   건조the organic phase was dried over sodium sulfate
9. 9
   여과the drying agent was filtered off
10. 10
    농축the filtrate was concentrated

실험 절차

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.

출처