1 3 dibromopropane the tide compound was as a yellow solid 78 7 mp 88 89 u00b0 c ms ei m e 274 276 m elemental analysis for c 9 h 11 brn 2 o 3 calc 39 d c 39 29 h 4 03 n 10 18 found c 39 71 h 3 91 n 10 27 a mixture of 2 2 chloro ethoxy 6nitro phenylamine 1a 3 0 g 13 8 mmol and benzylamine 9 0 g 84 0 mmol was heated neat at 100 110 u00b0 c for 6 hr the excess benzylamine was removed by distillation under vacuum 70 75 u00b0 c 0 1 mm the residue was poured into 1 n sodium hydroxide 300 ml and extracted with ethyl acetate 2 u00d7 300 ml the combined organic layer was washed with water 2 u00d7 300 ml and brine 300 ml the ethyl acetate layer was dried over anhydrous magnesium sulfate filtered and the solvent removed under vacuum to give 5 1 g of crude red oil purification by chromatography 500 g silica gel ethyl acetate 2 m nh 3 in methanol 20 1 afforded 3 54 g 89 3 of a red semi solid mp 33 60 u00b0 c ms ei m e 287 m elemental analysis for c 15 h 17 n 3 o 3 calc 39 d c 62 71 h 5 96 n 14 62 found c 62 64 h 6 04 n 14 23 1 dmso can be used as a solvent.