Formanilide and carbanilide from aniline and carbon dioxide
Earlier syntheses of formamides from the catalytic hydrogenation of CO 2 in the presence of amines were only successful for the preparation of dialkylformamides. After an analysis of the reason for the failure of the reaction using aniline as a starting material, formanilide has been prepared, for t...
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Published in | Tetrahedron letters Vol. 44; no. 13; pp. 2725 - 2727 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
24.03.2003
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | Earlier syntheses of formamides from the catalytic hydrogenation of CO
2 in the presence of amines were only successful for the preparation of dialkylformamides. After an analysis of the reason for the failure of the reaction using aniline as a starting material, formanilide has been prepared, for the first time, from CO
2, H
2 and aniline with the use of 1,8-diazabicyclo[5.4.0]undec-7-ene. Omission of the H
2 reductant causes the selectivity to switch to the production of carbanilide (1,3-diphenylurea).
Earlier methods for the reduction of CO
2 and amines to formamides have only been successful for dialkylamines. Now, a synthesis of formanilide from CO
2, H
2 and aniline has been designed. In the absence of H
2, carbanilide is formed. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/S0040-4039(03)00384-8 |