Sec-Butylamine → N-sec-Butyl-3,4-dimethyl-2,6-dinitroaniline

Participants

Reaction Steps

A mixture of 4-chloro-3,5-dinitro-o-xylene (140 grams, 0.61 mole), sec-butylamine (184 ml, 1.82 moles), and xylene (1400 ml) is brought to reflux. After refluxing overnight, the reaction mixture is cooled and filtered. The precipitate is washed with petroleum ether. The filtrate and washings are combined, washed with 500 ml. of 10% hydrochloric acid, and finally with 2 liters of water. The organic layer is separated and dried. Removal of the drying agent and the solvent leaves an orange oil which crystallizes with the addition of petroleum ether. A yellow orange solid (150.6 grams, 86.5%) with melting point 42° C. to 43° C. is collected.

Provenance & Evidence