p-Toluenesulfonic acid → (+/-) trans 1-(3,4-Dichlorophenylthio)-2-ethoxycarbonylaminoindane

Participants

Reaction Steps

A solution of (±) cis-2-ethoxy-3a,8b-dihydro-4H-indeno[2,1-d]oxazole (0.61 g, 3.0 mmol) in dry toluene (15 ml) was treated with 3,4-dichlorothiophenol (0.59 g, 3.3 mmol) and a catalytic amount of p-toluenesulfonic acid (0.15 ml of an anhydrous 0.1M solution of p-toluenesulfonic acid in benzene). The mixture was heated under nitrogen at 70°-75° C. for 3.5 h. The reaction was diluted with diethyl ether and washed with 5% NaOH (3×10 ml) followed by water (10 ml) and brine (10 ml). The organic phase was dried over Na2 SO4 and concentrated in vacuo to give a solid (1.0 g). Purification on a silica gel column using CHCl3 as eluant afforded the title compound as a colourless solid (0.81 g).

Provenance & Evidence