Hydrochloric Acid → 1-(2-Allylthio-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) and 2-(allylthio)-2-methylpropanal (3.85 g, 2.67×10-2 mol, 150 M %) were dissolved in 200 ml methanol. Glacial acetic acid (2.05 ml, 3.56×10-2, 200 M %) and sodium cyanoborohydride (3.36 g, 5.35×10-2 % mol, 300 M %) were then added. The reaction was stirred at room temperature for 18 hr, then 100 ml 0.50.5 M HCl was added and the mixture was extracted with 2×100 ml diethyl ether. The combined organic extracts were washed with 100 ml saturated NaHCO3, then with 100 ml saturated NaCl. The ether layer was dried over anhydrous Na2SO4, and the solvent was removed on the rotary evaporator. The crude product (6.7 g) was purified by filtration through a 600 ml sintered glass funnel filled silica bed, using 95% hexane/diethyl ether as the eluting solvent to give 4 g (70% yield) of 1-(2-allylthio-2-methylpropylamino)-2-(2-mercapto-2-methylpropylamino]benzene as a yellow oil.

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