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18.8.1.1.2.3 Variation 3: Transamidation of Ureas

DOI: 10.1055/sos-SD-018-00826

Sartori, G.; Maggi, R.Science of Synthesis, (200518670.

1,3-Diphenylurea (9) undergoes selective triethylamine-catalyzed replacement of one aromatic amine with a primary amine or morpholine in dimethylformamide affording 1-alkyl-3-phenylureas 10 (Scheme 5). The reaction does not proceed with sterically hindered secondary amines and aromatic amines bearing electron-withdrawing groups.[‌18‌] By carrying out the reaction in a sealed autoclave, not only primary but also secondary aliphatic amines react very well with 1,3-diphenylurea (9) in toluene without a catalyst giving 1,1-dialkyl-3-phenylureas 10 (Scheme 5).[‌19‌]

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