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ChemicalBook CAS DataBase List BENZYL ISOTHIOCYANATE
622-78-6

BENZYL ISOTHIOCYANATE synthesis

8synthesis methods
Benzyl isothiocyanate is synthesized by the following two methods: I) from Benzylamine via Thiuramdisulfide via Sodiumsalt with Iodine to Benzyl-isothiocyanate. 2) from Benzylamine and Thiocarbonyl chloride.
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Yield:622-78-6 97%

Reaction Conditions:

Stage #1:carbon disulfide;benzylamine in dimethyl sulfoxide for 0.25 h;Inert atmosphere;
Stage #2: with N-benzyl-trimethylammonium hydroxide in dimethyl sulfoxide for 2 h;Inert atmosphere;

Steps:

General procedure
General procedure: To a solution of amines (1 mmol) in DMSO, added carbon disulphide under nitrogen atmosphere and stirred for 15 min to afford compound 2. Further added triton-B after reaction mixture was stirred for 2 h to afford compound 3 (Scheme-I). After completion, extracted with ethyl acetate to yield isothiocyanates up to 80-99 %. The synthesized trithiocarbonates was subjected to 1H NMR, 13C NMR and mass spectroscopy for structure elucidation. The novel one pot synthesis yields good to excellent amount of isothiocyanates, both cyclic and acyclic substituent at room temperature.

References:

Singh, Neha;Khare, Richa [Asian Journal of Chemistry,2019,vol. 31,# 7,p. 1636 - 1638]

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