Synlett 2010(20): 3065-3067  
DOI: 10.1055/s-0030-1259072
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

o-Iodoxybenzoic Acid Mediated Oxidative Desulfurization of 1,3-Disubstituted Thioureas to Carbodiimides

Pramod S. Chaudhari, Prasad S. Dangate, Krishnacharya G. Akamanchi*
Department of Pharmaceutical Sciences and Technology, Institute of Chemical Technology, Matunga, Mumbai 400 019, India
Fax: +91(22)33611020; e-Mail: kgap@rediffmail.com;
Further Information

Publication History

Received 5 July 2010
Publication Date:
25 November 2010 (online)

Abstract

An efficient and mild oxidative desulfurization procedure using o-iodoxybenzoic acid has been developed for the synthesis of carbodiimides starting from easily synthesizable 1,3-disubstituted thioureas.

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15

Typical Procedure
Preparation of 1,3-Diphenyl Carbodiimide 2a
To a stirred solution of IBX (0.6 g, 2.19 mmol) and Et3N (0.6 mL, 4.38 mmol) in dry CH2Cl2 (10 mL) at 0 ˚C was added 1,3-diphenylthiourea (0.5 g, 2.19 mmol) portionwise over a period of 5 min. After completion of reaction, as indicated by TLC, reaction mixture was concentrated under vacuum, and the residue was extracted with hexane (2 × 15 mL). Pure product was isolated after evaporation of the hexane extract followed by column chromatography (SiO2, 60-120 mesh, eluent: hexane). Yield 0.38 g (90%), oily liquid. ¹H NMR (300 MHz, CDCl3): δ = 7.20 (m, 6 H), 7.31 (m, 4 H). ¹³C NMR (75 MHz, CDCl3): δ = 124, 125.2, 129.2, 136.2, 138.4. IR (KBr): 2140, 2110 cm. All synthesized compounds are known compounds. Characterization data are provided as Supporting Information.