Reaction #8507

Reaction equation

diisopropyl ether

water

compound ( 6 )

2-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridin-4-yl)methyl-1H-imidazole

hydrochloric acid

→

compound ( 12 )

2-Hydroxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridin-4-yl)methyl-1H-imidazole

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturecooled down
2. 2
   OtherThe aqueous layer was separated
3. 3
   ExtractionThe compound (12) was extracted with ethyl acetate (50 ml)
4. 4
   Washthe ethyl acetate layer was washed with water (30 ml)
5. 5
   ExtractionEach aqueous layer was extracted with ethyl acetate (20 ml)
6. 6
   OtherThe ethyl acetate layer was collected
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   Otherto yield oily residue
9. 9
   Otherfor crystallization
10. 10
    Filtrationfiltered
11. 11
    Washwashed with diisopropyl ether (30 ml)
12. 12
    Otherdried

Procedure

To the compound (6) was added concentrated aqueous hydrochloric acid (50 ml). The mixture was heated at 90° C. for 2 hours and then cooled down. To the mixture were added water (50 ml) and toluene (20 ml). The aqueous layer was separated and neutralized by 30% aqueous sodium hydroxide. The compound (12) was extracted with ethyl acetate (50 ml), and the ethyl acetate layer was washed with water (30 ml). Each aqueous layer was extracted with ethyl acetate (20 ml). The ethyl acetate layer was collected and concentrated under reduced pressure to yield oily residue. To the oily residue was slowly added diisopropyl ether (50 ml) for crystallization. The obtained slurry was stirred at room temperature for 30 minutes, filtered, washed with diisopropyl ether (30 ml) and dried to yield the compound (12) (10.4 g) as a white crystal. Yield from the compound (22):82%

Source