p-Toluenesulfonic acid → HCID 22618292, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of N-(3-chlorobenzoyl)-2-hydroxy-3-nitroaniline (4.5 g, 0.0117 mol), p-toluenesulfonic acid (0.30 g) and 50 ml of diphenyl ether were heated at 190° C. for 1 hour. The dark reaction mixture was dissolved in 100 ml CH2Cl2 and washed with saturated sodium bicarbonate and then water. The CH2Cl2 was evaporated and hexane was added, causing a brown solid to separate. The dark solid was filtered, dissolved in 75% CH2Cl2 in hexane and washed onto a silica gel column. Elution with this solvent, gave 3.3 g of the title compound. This material could be recrystallized from methanol to give 2-(3-chlorophenyl)-7-nitrobenzoxazole although it was pure enough from the chromatography to use for the next step without any further purification.

Provenance & Evidence