تفاعل #59894

معادلة التفاعل

2-(((4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzimidazole

3-chloroperbenzoic acid

sodium hydrogen carbonate

→

title compound

المردود 61.9%

2-(((4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole

المردود 61.9%

المذيبات

methanol

methanol

toluene

toluene

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise at −65° C. for 5 minutes in a nitrogen atmosphere
2. 2
   استخلاصthe mixture was extracted with ethyl acetate
3. 3
   تجفيفThe organic layer was dried over anhydrous sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was purified by silica gel column chromatography (NH silica gel: 20 g, elution solvent: dichloromethane, dichloromethane/methanol=10/1)
7. 7
   workup.ADDITIONThe fractions containing the title compound
8. 8
   أخرىwere collected with ethyl acetate
9. 9
   تركيزconcentrated
10. 10
    workup.ADDITIONTo the residue, diethyl ether was added
11. 11
    ترشيحThe resulting precipitate was collected by filtration
12. 12
    غسيلwashed with diethyl ether

الإجراء التجريبي

To a toluene (20 ml)-methanol (2 ml) solution of the 2-(((4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzimidazole (424 mg, 1.03 mmol) obtained in the step (11g), a toluene (1 ml)-methanol (1 ml) solution of 3-chloroperbenzoic acid (246 mg, 0.927 mmol as the content was regarded as 65%) was added dropwise at −65° C. for 5 minutes in a nitrogen atmosphere. The mixture was stirred for 45 minutes in the same conditions. To the reaction mixture, a saturated aqueous solution of sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (NH silica gel: 20 g, elution solvent: dichloromethane, dichloromethane/methanol=10/1). The fractions containing the title compound were collected with ethyl acetate and concentrated. To the residue, diethyl ether was added. The resulting precipitate was collected by filtration and washed with diethyl ether to obtain the title compound (274 mg, yield: 61.9%) as a white solid.

المصدر