Ethylenediamine → N-(2-Aminoethyl)-4-chlorobenzamide hydrochloride
Reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=O)=[CH:4][CH:3]=1.[CH2:13]([NH2:16])[CH2:14][NH2:15]>>[ClH:1].[NH2:15][CH2:14][CH2:13][NH:16][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:12][CH:11]=1Participants
3
Procedure
18.5 g of ethyl 4-chlorobenzoate and 24 g of ethylenediamine are stirred at 130° for 17 hours. The mixture is cooled to room temperature, evaporated, and the residue is treated with 200 ml of ethyl acetate. The insoluble N,N'-ethylenebis(4-chlorobenzamide) (2.3 g), m.p. 266°-268°, is filtered off under suction, and the filtrate is washed three times with 50 ml of water each time and evaporated. The residue is treated with 100 ml of 1N hydrochloric acid, the insoluble N,N'-ethylenebis(4-chlorobenzamide) (1.0 g) is filtered off under suction, and the filtrate is evaporated to dryness. The residue is then evaporated twice with 100 ml of ethanol/benzene each time and recrystallized from ethanol/ether. There are obtained 13.7 g of N-(2-amino-ethyl)-4-chlorobenzamide hydrochloride, m.p. 216°-217°.