反应详情

5.75 g (0.25 mole) of sodium are added piece by piece to a suspension of 21.46 g (0.04 mole) of alpha-(6-chloro-2,2-dimethyl-4H-1,3-benzodioxin-8-yl)-1-triphenylmethyl-1H-imidazole-4-methanol (prepared in Example 1.C.3.) in 2 liters of ammonia and 200 ml of toluene. stirring is maintained for 40 minutes, then the reaction mixture is decomposed by the addition of 6.42 g (0.12 mole) of ammonium chloride. 500 ml of toluene containing 10% of methanol are added thereto, the ammonia is evaporated and 500 ml of water are added thereto. The toluene phase is decanted off, dried over anhydrous sodium sulfate and then distilled. The residue, containing triphenylmethane, is partly dissolved in 50 ml of water containing 3.3 ml of concentrated hydrochloric acid and the suspension obtained is extracted with diethyl ether. The aqueous phase is subsequently adjusted to pH 8 by the addition of sodium bicarbonate, then extracted with dichloromethane. Subsequently, the solvent is removed by distillation to give 3.5 g of alpha-(2,2-dimethyl-4H-1,3-benzodioxin-8-yl)-1H-imidazole-4-methanol. Yield: 33% of theory. The product formed a hydrochloride (recrystallizable in a 1:1 v/v ethanol-diethyl ether mixture) which has a glassy appearance and which does not have a sharp melting point.

1. temperatureis maintained for 40 minutes
2. customthe ammonia is evaporated
3. addition500 ml of water are added
4. customThe toluene phase is decanted off
5. dry with materialdried over anhydrous sodium sulfate
6. distillationdistilled
7. additionThe residue, containing triphenylmethane
8. dissolutionis partly dissolved in 50 ml of water containing 3.3 ml of concentrated hydrochloric acid
9. customthe suspension obtained
10. extractionis extracted with diethyl ether
11. additionThe aqueous phase is subsequently adjusted to pH 8 by the addition of sodium bicarbonate
12. extractionextracted with dichloromethane
13. customSubsequently, the solvent is removed by distillation