反応 #161342

反応方程式

ammonia

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

2-aminobenzenethiol

→

title compound

収率 1.9%

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

収率 1.9%

反応条件

後処理

1. 1
   その他A 4-neck flask (50 mL) equipped
2. 2
   温度with reflux condenser
3. 3
   温度to cool to room temperature
4. 4
   温度this was cooled in ice (0 to 5° C.)
5. 5
   その他to give approx. pH 9
6. 6
   workup.DISTILLATIONAfter distilling off the solvent under reduced pressure
7. 7
   抽出the brown viscous residue was extracted with ethyl acetate
8. 8
   乾燥this was dried over anhydrous magnesium sulfate
9. 9
   その他The residue obtained
10. 10
    workup.DISTILLATIONafter again distilling off the solvent under reduced pressure
11. 11
    その他was purified by PTLC

実験手順

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.

出典