• Indah Purnama Sary Jember University
  • Siswandono Airlangga University
  • Tutuk Budiati Airlangga University


N-phenylbenzamide, 1, 3-diphenylthiourea, Imino alcohol-amide tautomerism, Rearrangement intermediate


Objective: N-phenylbenzamides are important and biologically active compounds. N-phenylbenzamides have been synthesized by some routes. An attempt has been made to find out the new route to synthesize N-phenylbenzamides.

Methods: The reaction was carried out by reacting substituted benzoyl chlorides with 1,3-diphenylthiourea in the presence of triethylamine in THF at 70 °C. After 4hr the product was purified and identified.

Results: An excellent and pure yield of N-phenylbenzamides was obtained by reacting substituted benzoyl chlorides with 1,3-diphenylthiourea. The proposed mechanism follows imino alcohol-amide tautomerism and suggests the involvement of rearrangement intermediate.

Conclusion: 1,3-diphenylthiourea is inexpensive commodity chemical and it is found to be the useful reagent for the direct conversion to N-phenylbenzamide. The proposed mechanism follows imino alcohol-amide tautomerism and suggests the involvement of rearrangement intermediate. The synthesis gave pure, high yield, and the one and only isolated product.



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How to Cite

Sary, I. P., Siswandono, and T. Budiati. “N-PHENYLBENZAMIDE SYNTHESIS BY NUCLEOPHILIC SUBSTITUTION WITH 1,3-DIPHENYLTHIOUREA”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 7, no. 3, Mar. 2015, pp. 481-2, https://journals.innovareacademics.in/index.php/ijpps/article/view/3952.



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