تفاعل #161342

معادلة التفاعل

ammonia

2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt

2-aminobenzenethiol

→

title compound

المردود 1.9%

5-(benzothiazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole

المردود 1.9%

ظروف التفاعل

المعالجة

1. 1
   أخرىA 4-neck flask (50 mL) equipped
2. 2
   درجة الحرارةwith reflux condenser
3. 3
   درجة الحرارةto cool to room temperature
4. 4
   درجة الحرارةthis was cooled in ice (0 to 5° C.)
5. 5
   أخرىto give approx. pH 9
6. 6
   workup.DISTILLATIONAfter distilling off the solvent under reduced pressure
7. 7
   استخلاصthe brown viscous residue was extracted with ethyl acetate
8. 8
   تجفيفthis was dried over anhydrous magnesium sulfate
9. 9
   أخرىThe residue obtained
10. 10
    workup.DISTILLATIONafter again distilling off the solvent under reduced pressure
11. 11
    أخرىwas purified by PTLC

الإجراء التجريبي

A 4-neck flask (50 mL) equipped with reflux condenser was charged with 2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt (see Working Example 4-3) (0.28 g, 1.08 mmol), 2-aminobenzenethiol (0.14 g, 1.08 mmol) and polyphosphoric acid (approx. 11 g), and this was heated to 150° C. and stirred for 17 hours. After being allowed to cool to room temperature, this was cooled in ice (0 to 5° C.), and concentrated aqueous ammonia (28%) was added to the liquid to give approx. pH 9. After distilling off the solvent under reduced pressure, the brown viscous residue was extracted with ethyl acetate, this was dried over anhydrous magnesium sulfate. The residue obtained after again distilling off the solvent under reduced pressure was purified by PTLC to yield the title compound (0.007 g, 1.8% yield) as greenish-pale yellow crystals.

المصدر