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Synthesis and conversions of amidomercaptals

Communication 4. On the reactions of formamidomercaptals with isocyanates and isothiocyanates

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Conclusions

  1. 1.

    The reactions of amidomercaptals with aryl isocyanates give 1,3-diaryl-5-dialkylamino-5-alkylmercaptohydantoins; in addition to these, the reaction products include S-alkyl esters of thiolcarbamic acid and S-alkyl esters of 2,4-diarylthiolallophanic acid.

  2. 2.

    We have developed a simple method for obtaining S-alkyl esters of 2,4-diarylthiolallophanic acid by reacting 2 M of aryl isocyanate with 1 M of mercaptan in the presence of triethylamine.

  3. 3.

    We have studied the reactions of amidomercaptals with aryl isothiocyanates in the presence of alcohol, the products being S,S′-alkyl esters of aryl imidodithiocarboxylic acid. It is shown that in the presence of alcohol amidomercaptals can alkylate the C=S bond in aryl isothiocyanates and thiobenzanilide.

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Literature cited

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 576–583, March, 1968.

For Communication 3, see [1].

As a result of a decision by the Conference of Chief Editors of Journals of the Academy of Sciences of the USSR on July 12, 1962, this article is published as a Dissertation of I. A. Ivanova.

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Ivanova, I.A., Fedorov, B.P. & Stoyanovich, F.M. Synthesis and conversions of amidomercaptals. Russ Chem Bull 17, 559–564 (1968). https://doi.org/10.1007/BF00911611

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Keywords

  • Alcohol
  • Ester
  • Triethylamine
  • Isothiocyanates
  • Isocyanate