Benzyl Bromide → 1-Acetamido-4-benzyloxy-2-nitrobenzene

Participants

Reaction Steps

2.94 G. of 1-acetamido-4-hydroxy-2-nitrobenzene, 4.2 g. anhydrous potassium carbonate and 5.13 g. benzyl bromide were refluxed overnight with stirring in 100 ml. acetone. Evaporation and extraction of the residue with dichloromethane affords 1-acetamido-4-benzyloxy-2-nitrobenzene. This latter compound is treated with sodium hydroxide in methanol, warmed briefly on a steam bath for about 15 minutes until the reaction is complete, diluted with water and extracted with dichloromethane to afford 1-amino-4-benzyloxy-2-nitrobenzene. This latter compound is treated for 4 hours in a refluxing hydrochloric acid acidified mixture of 160 ml. methanol and 40 ml. water with 4 g. iron powder (added in two portions) and 1 g. ferrous sulfate. The mixture is poured into 150 ml. concentrated ammonia, then extracted with chloroform to afford 1,2-diamino-4-benzyloxybenzene. This latter compound is treated in accordance with the fourth paragraph of Example XV to afford 4 -benzyloxy-1,2-bis(3-methoxycarbonyl-2-thioureido)benzene.

Provenance & Evidence