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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Bibliographic Details
Published inTetrahedron letters Vol. 44; no. 13; pp. 2725 - 2727
Main Authors Munshi, Pradip, Heldebrant, David J., McKoon, Erin P., Kelly, Patrick A., Tai, Chih-Cheng, Jessop, Philip G.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 24.03.2003
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
METHYL FORMATE
FORMIC-ACID
CATALYSIS
N,N-DIMETHYLFORMAMIDE
HYDROGENATION
FORMAMIDES
URETHANES
AMINES
COMPLEXES
CO2
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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.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)00384-8