반응 #59856

반응 방정식

2-mercaptobenzimidazole

(3-methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl) methanol

triethylamine

methanesulfonyl chloride

sodium hydrogen carbonate

→

title compound

수율 79.8%

2-(((3-methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl)thio)-1H-benzimidazole

수율 79.8%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The mixture was cooled on ice in a nitrogen atmosphere
2. 2
   온도cooling
3. 3
   workup.STIRRINGstirred at room temperature overnight
4. 4
   추출extracted with ethyl acetate
5. 5
   세척The organic layer was washed with a saturated saline solution
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   농축The filtrate was concentrated under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
10. 10
    workup.ADDITIONAfter silica gel was added to the solution
11. 11
    농축the solution was concentrated
12. 12
    세척The dried residue was subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1→0/1)

실험 절차

The (3-methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl) methanol (450 mg, 1.6 mmol) obtained in the step (3e) was mixed with tetrahydrofuran (10 ml). The mixture was cooled on ice in a nitrogen atmosphere. To this, triethylamine (0.446 ml, 3.2 mmol), and methanesulfonyl chloride (0.186 ml, 2.4 mmol) were added and stirred for 50 minutes under ice-cooling. To the reaction mixture, 2-mercaptobenzimidazole (240 mg, 1.6 mmol) was added and stirred at room temperature overnight. To the reaction mixture, an aqueous solution of sodium hydrogen carbonate was added and extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate. After silica gel was added to the solution, the solution was concentrated. The dried residue was subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1→0/1) to obtain the title compound (528 mg, 79.8%) as a colorless viscous oil.

출처