Unsatd. carbodiimide cpds. used in prepn. of pharmaceuticals - prepd. by reacting isothiocyanate cpds. with amine(s) and desulphurising resulting thiourea

摘要

New unsatd. carbodiimides are of formula R1-N=C=N-R2 (I) (where R1 and R2 and each an opt. unsatd. (cyclo)aliphatic residue, either of which may contain a hetero atom, provided that =1 or R1 and R2 is an olefinically unsatd. aliphatic residue). (I) are useful as intermediates for plastics and pharmaceuticals. They undergo the usual addition reactions of carbodiimides (e.g. qith water to give ureas, with alcohols or phenols to give trisubstd. isoureas, with H2S to give thioureas, with acids to give N-acyl-ureas, or with malonic acid to give barbituric acid derivs), the addition prod. carrying =1 unsatd. residue. (I) may also be (co)polymerised via the olefinic unsaturation. Specific (I) include N-methallyl-N'-tert-butyl-carbodiimide. In an example, this is prepd. by reacting methallyl isothiocyanate with tert-butylamine in petroleum ether and desulphurising the resulting N-methallyl-N'-tertbuytyl-thiourea with a soln. of Cl2 in aq. NaOH.