Calcium Carbonate → 3-Chloropropyl (4-hydroxy-2-nitrophenyl)carbamate

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[CH:8][C:9]=1[NH2:10])([O-:3])=[O:2].C(=O)([O-])[O-].[Ca+2].Cl[C:18]([O:20][CH2:21][CH2:22][CH2:23][Cl:24])=[O:19]>C(COC)OC>[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[CH:8][C:9]=1[NH:10][C:18](=[O:19])[O:20][CH2:21][CH2:22][CH2:23][Cl:24])([O-:3])=[O:2]

Participants

Procedure

77 g (0.5 mole) of 3-nitro-4-aminophenol are dissolved in 200 ml of dimethoxy ethane, 27 g of calcium carbonate are added, and 80 g (0.51 mole) of γ-chloropropyl chloroformate are added dropwise at 70° C. After 1 hour, the reaction mixture is filtered hot and the filtrate is stirred into 700 ml of ice-water, after which 128 g (93%) of the desired compound precipitate. The melting point is 103°-105° C., and after recrystallisation from toluene is 106° C.