caa a22 4500 469038543 CHVBK 20180323132803.0 cr unu---uuuuu 170328e19920601xx s 000 0 eng 10.1007/BF00816855 doi (NATIONALLICENCE)springer-10.1007/BF00816855 The synthesis of N-substituted ureas I: The N-alkylation of ureas [Elektronische Daten] [Kurt Hackl, Heinz Falk] Zur Synthese N-substituierter Harnstoffe I: Die N-Alkylierung von Harnstoffen Summary: Urea and N-alkylureas are N′-alkylated in low yields using aprotic dipolar solvents, like dimethylsulfoxide, solid potassium hydroxide, and alkyl halides. Phase transfer catalysis with tetrabutylammonium chloride in refluxing toluene results in high yield regioselective N′-alkylation of N-alkylureas by means of alkyl halides, tosylates, mesylates, and sulfates as alkylating agents and alkali hydroxide as the base — however, N-arylureas are not alkylated under these conditions. Kinetic studies point to a SN2 type reaction which obeys the Kornblum rule. Springer-Verlag, 1992 N-substituted Ureas nationallicence N-Alkylation nationallicence Kornblum rule nationallicence Regioselectivity nationallicence Phase transfer nationallicence Hackl Kurt Institut für Chemie, Johannes Kepler Universität Linz, A-4040, Linz, Austria aut Falk Heinz Institut für Chemie, Johannes Kepler Universität Linz, A-4040, Linz, Austria aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 123/6-7(1992-06-01), 599-606 0026-9247 123:6-7<599 1992 123 706 https://doi.org/10.1007/BF00816855 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00816855 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Hackl Kurt Institut für Chemie, Johannes Kepler Universität Linz, A-4040, Linz, Austria aut NATIONALLICENCE 700 1- Falk Heinz Institut für Chemie, Johannes Kepler Universität Linz, A-4040, Linz, Austria aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 123/6-7(1992-06-01), 599-606 0026-9247 123:6-7<599 1992 123 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer