Abstract
A study on the thermal dissociation of tolbutamide (I) in a series of 12 primary aliphatic alcohols, C1to C18, and in polyethylene glycol 400 USP at 80° is presented.It is shown that the compound dissociates in only one of two possible fashions, i.e., only to give butylamine and p-toluenesulfonyl isocyanate.In all cases, an N-(p-toluenesulfonyl)carbamate, formed by reaction of the sulfonyl isocyanate with the alcohols, was present in the equilibrium mixture. p-Toluenesulfonamide and alkyl N-butylcarbamates, arising from the other possible dissociation, were never evidenced.The results are consistent with a mechanism involving, as the first step, a preferential conversion of I into one of two possible tautomeric forms.
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