M-Phenylenediamine → HCID 21434867, compound

Participants

Reaction Steps

Isobutyl isothiocyanate (16 g.) is added dropwise with stirring to a solution of m-phenylenediamine (17 g.) in methylene chloride (500 ml.) at room temperature. After 16 hours the solution is concentrated until crystallization begins. The mixture is diluted with benzene, and the product is filtered off, washed with benzene and dried. The 1-isobutyl-3-m-aminophenylthiourea thus obtained (23 g.) is dissolved in ethanol (250 ml.) saturated with ammonia gas, and stirred for 48 hours at room temperature with yellow mercuric oxide (28.2 g.). The mixture is filtered, the solids washed thoroughly with boiling ethanol and the combined filtrate and washings are evaporated to dryness. The residue is dissolved in a little methanol, treated with excess saturated ethereal hydrogen chloride and a large volume of dry ether. A red oil separates, which is triturated with fresh ether until solid, and the solid is filtered off and crystallized from methanol/ethyl acetate, to give 1-isobutyl-3-m-aminophenylguanidine dihydrochloride, m.p. 215° C.

Provenance & Evidence