Benzoic Acid → t-Butyl carbanilate

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Following Example 12 and replacing the nitromethane by 75 ml of acetonitrile, 4.75 g of N3 -SPO were obtained, with a 91% yield. A sample of 1.3 g of N3 -SPO was taken with 0.61 g of benzoic acid, 0.7 ml of triethylamine (TEA) in 16 ml of tert-butanol. The mixture was stirred under reflux for 6 hours; the IR of the thus obtained solution showed the absence of the N3 band. Water was added to the solution, it was stirred and 25 ml of benzene was added. The solution was washed with water, a saturated bicarbonate solution and finally with water. The benzene was dried over sodium sulphate. The solution was evaporated to dryness at reduced pressure. The solid obtained was recrystallised in n-hexane to give tert-butyl phenylcarbamate, melting point 134°-136° C. Yield 70%. IR: carbonyl band at 1690 cm-1 and NH band at 3320 cm-1.

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