Acetic Acid → 1-[2-(3-Butenylthio)-2-methylpropylamino]-2-(2-mercapto-2-methylpropylamino)benzene

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Reaction Steps

2-Amino-1-(2-mercapto-2-methylpropylamino)benzene (3.5 g, 1.78×10-2 mol, 100 M%) and 2-(3-butenylthio)-2-methylpropanal (4.23 g, 2.67×10-2 mol, 150 M%) were dissolved in 200 ml methanol. Glacial acetic acid (2.05 ml, 3.56×10-2 mol, 200 M%) and sodium cyanoborohydride (3.36 g, 5.35×10-2 mol, 300 M%) were then added. After 17 hours, the reaction was quenched by the addition of 100 ml 0.5 N HCl. The acidic solution was then extracted with 2×100 ml diethyl ether. The combined organic extracts were washed with 100 ml saturated NaHCO3, followed by 100 ml saturated NaCl. The ether layer was then dried over anhydrous Na2SO4. The solvent was removed on the rotary evaporator, and the residue was purified by filtration through a 600 ml sintered-glass funnel silica bed, using 90% hexane/diethyl ether as the eluting solvent, to give 5 g (84% yield) 1-[2-(3-butenylthio)-2-methylpropylamino]-2-(2-mercapto-2-methylpropylamino)-benzene as a yellow oil.

Provenance & Evidence