Ethyl Acetate → 5-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

Participants

Reaction Conditions

Reaction Steps

To 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.20 g, 0.646 mmol), triethyl orthoformate (5 mL) was added a catalytic amount of p-toluenesulfonic acid monohydrate, and this was heated to 100° C. for 1.5 hours. The reaction mixture was cooled, ethyl acetate and water added, and this was extracted. This was washed with water, dried over magnesium sulfate, and after concentration the precipitated crystals were filtered off. These were washed with a hexane/ethyl acetate mixture solution, and dried to yield the title compound (65 mg, 31.5% yield) as light reddish-brown crystals.

Provenance & Evidence