Ammonia → HCID 22096854, compound

Participants

Reaction Steps

3-[N,N-Bis(2-chloroethyl)amino]nitrobenzene (2.0 g; 7.6 mmol) was dissolved in 35 ml of concentrated hydrochloric acid, followed by the addition of 6.9 g (30.6 mmol; 4.0 equivalents) of tin(II) chloride dihydrate. The resultant mixture was stirred under heating for 1 hour over an oil bath controlled at 100° C. The reaction mixture was allowed to cool down to room temperature and then diluted with water. The resulting mixture was basified with concentrated aqueous ammonia and then extracted twice with ethyl acetate. The extracts were combined, dried over sodium sulfate and then concentrated under reduced pressure. The residue was added with 4N hydrochloric acid/dioxane, followed by concentration. The residue was crystallized from a mixed solvent of a small amount of methanol and ethyl ether, whereby 1.97 g (7.3 mmol) of the title compound were obtained as yellow crystals (yield: 96.1%).

Provenance & Evidence