p-Toluenesulfonic acid → HCID 66759851, compound

Participants

Reaction Steps

A mixture of 3-bromo-2-tert-butylsulfanyl-5-nitro-benzaldehyde oxime (1.98 g, 5.97 mmol) and p-toluenesulfonic acid (567 mg, 2.98 mmol) in n-butanol (20 mL) was heated to reflux for 16 h. The reaction mixture was cooled and concentrated. The residue was treated with water followed by saturated sodium bicarbonate solution and then was extracted with dichloromethane (3×20 mL). The combined organic fractions were washed with water, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (20% ethyl acetate:hexanes) afforded 1.0 g (65%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 9.21 (s, 1H), 8.95 (s, 1H), 8.59 (s, 1H).

Provenance & Evidence