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Synthesis 1986; 1986(10): 817-820
DOI: 10.1055/s-1986-31789
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Preparation and Reactions of N-Alkyl(Aryl), N-Isothiocyanatomethyl Carboxamides. Synthesis of 1,3,5-Thiadiazepin-6-ones

András Vass* , Gábor Szalontai
  • *Research Institute for Heavy Chemical Industries, H- 8200 Veszprém, Pf. 160, Hungary
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Publication Date:
20 August 2002 (online)

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N-Alkyl(aryl),N-isothiocyanato carboxamides 3 are prepared by the reaction of the corresponding 2-chloroacetamides 1 with potassium thiocyanate. In the case of N-aryl substitution the intermediate thiocyanates 2 could be isolated. These thiocyanates isomerize to isothiocyanates 3 at different rates depending on aryl substituents, temperature and solvents. The reaction between 3k and a nucleophilic agent (e.g. methanol, isopropylthiol, sodium hydrogensulfide, or ethyl malonate) results in the corresponding 1,3,5-thiadiazepin-6-ones, 5 by ring closure.