Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].Cl.ClC1[CH:13]=[C:14](C=CC=1)[NH2:15].O1CCNC1=O.C(=O)=O>CCOCC.O>[Cl:2][C:3]1[CH:4]=[C:5]([NH:6][CH2:13][CH2:14][NH2:15])[CH:7]=[CH:8][CH:9]=1
Gaseous hydrogen chloride was reacted with m-chloroaniline in ether at 0° C. to prepare the m-chloroaniline hydrochloride. This reactant (65.6 g, 0.4 mole) was then intimately mixed with 2-oxazolidinone by grinding with a mortar and pestle. The ground mixture was then added to a 250 ml flask equipped with a mechanical stirrer and gas vent. The flask was heated in an oil bath to 160° C. with stirring. The solid mixture melted and CO2 evolution commenced in about 15 minutes. Heating was continued for about six hours whereupon the flask was cooled and the contents dissolved in water and filtered. The filtrate was then basified with aqueous caustic causing a yellow oil to separate. Extraction with methylene chloride, drying and distillation under vacuum gave 55 g (80 percent yield) of N-(3-chlorophenyl)-1,2-ethanediamine.
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