Synthesis. -Optimized syntheses of 4-isothiocyanatomethylpyridine (IX) and title ester (VI), side product in the original synthesis of (IX), are developed. Both compounds appear to be appropriate precursors for the preparation of thiourea derivative (VIII). -(SARHAN*, A. E.; JOERGENSEN, P. T.; PEDERSEN, E. B.; Synth. Commun. 35 (2005) 18, 2475-2480; Dep. Med.
The synthesis of 4-isothiocyanatomethyl-pyridine 4 in 36% yield by Hasegawa and Kotani (Japanese patent 49088878, 1974) has spurred us to investigate this preparation in detail. In addition to this compound, 4-isothiocyanatomethylene-4H-pyridine-1-carboxylic acid ethyl ester 3 can be isolated. The synthesis of both compounds 3 and 4 were optimized to 75% and 50% yield respectively. Reaction of compound 3 with methylamine gave thiourea derivatives 5, the same product obtained on reacting 4-isothiocyanatomethyl-pyridine 4 with methylamine. We succeed in adjusting the reaction conditions to obtain high yield either from compound 3 or isothiocyanate derivatives 4.
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