Sodium Hydroxide → Dimethyl-(4-nitro-2-oxazol-2-yl-phenyl)-amine

Participants

Reaction Steps

A solution of N-(2,2-dimethoxyethyl)-2-dimethylamino-5-nitro benzamide (1.1 g, 3.7 mmol) in methane sulphonic acid (5 ml) was added to a slurry of phosphorus pentoxide (2.6 g, 18.51 mmol) in methane sulphonic acid (15 ml) and refluxed overnight. The reaction mixture was cooled to room temperature, poured onto ice water, and then basified with dilute sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to a residue. Purification by chromatography over silica gel using 5-30% ethyl acetate/pet ether gave dimethyl-(4-nitro-2-oxazol-2-yl-phenyl)-amine (150 mg, 60%) as solid.

Provenance & Evidence