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Synlett 2010(7): 1104-1106
DOI: 10.1055/s-0029-1219566
DOI: 10.1055/s-0029-1219566
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Symmetrical Ureas by (Diacetoxyiodo)benzene-Induced Hofmann Rearrangement
Further Information
Received
22 January 2010
Publication Date:
02 March 2010 (online)
Publication History
Publication Date:
02 March 2010 (online)
![](https://www.thieme-connect.de/media/synlett/201007/lookinside/thumbnails/10.1055-s-0029-1219566-1.jpg)
Abstract
Amides undergo Hofmann rearrangement by treatment with (diacetoxyiodo)benzene (DAIB) to provide symmetrical ureas in a simple and robust transformation.
Key words
Hofmann rearrangement - ureas - carbamates - diacetoxyiodobenzene
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References and Notes
Representative Procedure (Table 1, Entry 1): A solution of benzamide (121 mg, 1.00 mmol), PhI(OAc)2 (DAIB; 419 mg, 1.30 mmol) and H2O (54 µL, 3.00 mmol) in CH2Cl2 (10 mL) was stirred at ambient temperature for 16 h. The resulting solution was stirred at 40 ˚C for 1 h, then the solution was concentrated under vacuum and the remaining residue was purified by column chromatography on silica gel (hexane-EtOAc, 3:1) to yield the corresponding urea as a colorless solid (52.4 mg, 49%).