Benzyl isothiocyanate Benzylamine

Enterobacter cloacae convert benzyl isothiocyanate to benzylamine and hydrogen sulphide... 

Benzyl isothiocyanate was identified in aqueous extracts of C. sativa foliage by Lovett and Duffield ( ). Tang, Bhothipaksa and Frank ( ) showed that E. cloacae was capable of degrading benzyl isothiocyanate to hydrogen sulfide and benzylamine. Tests were, accordingly, carried out with incubated leaf washings of Camelina and showed the presence of hydrogen sulfide and... 

A soln. of GS2 in abs. ether added dropwise with stirring and ice-salt cooling to a soln. of 2 moles benzylamine in the same solvent, the precipitated benzyl-ammonium dithiocarbamate removed by filtration, dissolved in benzene, a soln. of pyrocatechyl phosphorotrichloridate in the same solvent added dropwise with stirring and ice-cooling, then refluxed 1 hr. on a water bath benzyl isothiocyanate. Y 84%. F. e., also by POGI3 instead of pyrocatechyl phosphorotrichloridate with somewhat lower yields, s. D. Martin, E. Beyer, and H. Gross, B. 98, 2425 (1965). 

Coned. HCl added to l-benzyl-3-ferf-butylthiourea prepared from benzylamine and fert-butyl isothiocyanate (s. Synth. Meth. 18, 555), warmed 5 min. at 90-95° on a water bath -> 1-henzylthiourea. Y 96. F. e., also removal of tert-snayl groups, s. G. V. Nair, Indian J. Ghem. A, 516 (1966). 

A soln. of p-bromophenyl isothiocyanate in alcohol allowed to react gradually with an equimolar amount of aq. NaHS, 3 moles 37%-formalin soln. and aq. benzylamine sulfate added, stirred 0.5 hr. at room temp. 5-benzyl-3-p-bromophenyltetrahydro-l,3,5-thiadiazine-2-thione. Y 85%. P. Kristidn and J. Bernat, Tetrah. Let. 1968, 679. 

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