반응 #67082

반응 방정식

chloro(3-chlorobenzyl)zinc tetrahydrofuran

4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}thiomorpholine 1,1-dioxide

tetrahydrofuran

→

4-{[2-(3-chlorobenzyl)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}thiomorpholine 1,1-dioxide

용매

water

반응 조건

후처리

1. 1
   추출the aqueous layer was extracted with ethyl acetate
2. 2
   세척The organic layer was washed with water and saturated brine
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)
7. 7
   workup.ADDITIONTo the obtained pale yellow solid were added 1,4-dioxane (10 mL) and 1-methylpiperazine (0.16 mL)
8. 8
   workup.STIRRINGby stirring at room temperature for 6 hours
9. 9
   workup.ADDITIONTo the reaction mixture was added water
10. 10
    추출the aqueous layer was extracted with ethyl acetate
11. 11
    세척The organic layer was washed with water and saturated brine
12. 12
    건조dried over anhydrous magnesium sulfate
13. 13
    여과filtered
14. 14
    농축concentrated
15. 15
    기타The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)
16. 16
    세척The obtained white solid was washed with ethanol

실험 절차

To a mixture of 4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}thiomorpholine 1,1-dioxide (500 mg), dichlorobis(triphenylphosphine)nickel (II) (190 mg), tetrahydrofuran (10 mL) was added a 0.5 M chloro(3-chlorobenzyl)zinc tetrahydrofuran solution (3.2 mL), followed by stirring at room temperature for 6 hours. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate). To the obtained pale yellow solid were added 1,4-dioxane (10 mL) and 1-methylpiperazine (0.16 mL), followed by stirring at room temperature for 6 hours. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate). The obtained white solid was washed with ethanol to obtain 4-{[2-(3-chlorobenzyl)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}thiomorpholine 1,1-dioxide (212 mg) as a white solid.

출처