Ethanol → 4,5-Dimethyl-3-nitro-2-N-pentan-3-ylbenzene-1,2-diamine

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Reaction Conditions

Reaction Steps

N-(1-Ethylpropyl)-2,6-dinitro-3,4-xylidine (100 g.) is dissolved in 2500 ml. of ethanol and a solution of sodium sulfide nonahydrate (240 g.) and sodium bicarbonate (84 g.) in 500 ml. of water is added at 25°-42° C. The mixture is heated to 65° C. and held at 60°-65° C. for 3 hours. The mixture is then poured into water and extracted 3 times with 1 liter portion of ether. The ether extracts are combined and dried over magnesium sulfate. Removal of the drying agent and solvent leaves a dark solid which is recrystallized 3 times from hexane and then 3 times from hexane-ethanol. The product (35.0 g.), an orange solid, has m.p. 80°-82° C. Analysis Calcd. for C13H21N3O2 : C, 62.12; H, 8.41; N, 16.71. Found: C, 62.41; H, 8.33; N, 16.47.

Provenance & Evidence