2-Nitrobenzyl alcohol → o-Nitrobenzyl benzylcarbamate

Participants

Reaction Steps

10 ml of toluene, 5.75 g of 2-nitrobenzyl alcohol and 5 g of benzyl isocyanate were heated to reflux for 3 hours in a nitrogen atmosphere. Following cooling of the mixture, 50 ml of toluene was added. This reaction solution was washed several times with water, and was then dehydrated with sodium sulfate. The sodium sulfate was then filtered out, and the solvent was removed from the filtrate by means of a rotary evaporator. The solid obtained was recrystallized from a hexane-toluene mixed solvent, producing 7.3 g of o-nitrobenzyl benzylcarbamate in the form of plate yellow crystals. This compound had a melting point of 110° to 111° C., and the infrared absorption spectrum was 3308 cm-1 : N--H, 1696 cm-1 : C=O, 1520 cm-1 : N--O.

Provenance & Evidence