O-Phenylenediamine → 2-Amino-1-(2-mercapto-2-methylpropylamino)benzene

Participants

Reaction Conditions

Reaction Steps

o-Phenylenediamine (15.31 g, 1.42×10-1 mol, 100M %) and 12.46 g (1.42×10-1 mol, 100M %) isobutylene sulfide (Snyder et al, J Am Chem Soc 69: 2672-2674, 1947) were mixed in a Parr bomb and heated in an oven at 80° C. for 18 hr. The bomb was cooled to room temperature and then opened. The crude brown oil contained some solid. The mixture was dissolved in 150 ml ether (some white solid did not dissolve), washed with saturated aqueous NaCl solution, and the solvent was removed on the rotary evaporator. The oily residue was placed on flash silica in a 600 ml sintered glass funnel and eluted with 500 ml portions of hexane, 90% hexane/ether, twice with 80% hexane/ether and twice with 50% hexane/ether. Evaporation of the first 50:50 hexane/ether fraction gave 7.36 g (26.5%) of 2-amino-1-(2-mercapto-2-methylpropylamino)benzene as a waxy crystalline product, mp 38°-40° C.

Provenance & Evidence