تفاعل #59885

معادلة التفاعل

sodium hydrogen carbonate

toluene

2-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)thio)-1H-benzimidazole

3-chloroperbenzoic acid

→

title compound

المردود 76.2%

2-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole

المردود 76.2%

المذيبات

methanol

toluene methanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added at −70° C. in a nitrogen atmosphere
2. 2
   درجة الحرارةAfter the mixture was warmed to room temperature
3. 3
   استخلاصthe mixture was extracted with ethyl acetate twice
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىThe residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate, ethyl acetate/methanol=9/1)
8. 8
   workup.ADDITIONFractions containing the title compound
9. 9
   أخرىwas collected by use of ethyl acetate
10. 10
    تركيزconcentrated
11. 11
    workup.ADDITIONAfter diethyl ether was added to the residue
12. 12
    workup.DISTILLATIONthe solvent was distilled off

الإجراء التجريبي

To a toluene (30 ml)/methanol (3 ml) solution of the 2-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)thio)-1H-benzimidazole (290 mg, 0.73 mmol) obtained in the step (9h), a toluene/methanol (10:1) solution of 3-chloroperbenzoic acid (174 mg, 0.65 mmol as the content was regarded as 65%) was added at −70° C. in a nitrogen atmosphere. After the mixture was stirred at −50° C. for one hour, a saturated aqueous solution of sodium hydrogen carbonate was added. After the mixture was warmed to room temperature, the mixture was extracted with ethyl acetate twice. Organic layers were combined and dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate, ethyl acetate/methanol=9/1). Fractions containing the title compound was collected by use of ethyl acetate and concentrated. After diethyl ether was added to the residue, the solvent was distilled off to obtain the title compound (230 mg, yield: 76.2%) as a white solid.

المصدر