Reference

Procedure for the production of N,N'-Carbonyldiazole from azolide salts

Procedure for the production of N,N'-Carbonyldiazole from azolide salts. Scherer, Johannes; Klausener, Alexander; Soellner, Robert (Bayer A.-G., Germany). Ger. Offen. DE 10035011 A1 31 Jan 2002, 8 pp. (German). (Germany). CODEN: GWXXBX. CLASS: ICM: C07D233-60. ICS: C07D235-08; C07D231-12; C07D231-56; C07D249-08; C07D249-18. APPLICATION: DE 2000-10035011 19 Jul 2000. DOCUMENT TYPE: Patent CA Section: 28 (Heterocyclic Compounds (More Than One Hetero Atom)) N,N'-Carbonyldiazoles I [X1, X2, X3 = CR1, N; R1 = H, C1-6-alkyl; R2 = H; R1R2 = CH:CHCH:CH] are obtained in a particularly advantageous way, if one converts appropriate azolide salts, e.g., II [M = alkali metal, ammonium ion, phosphonium ion], with phosgene in aroms. or a ether as solvent and characterized by the azolide salts II being preferably made in a new procedure from an azole II [M = H], which one converts with a compd., M'R7 [M' = alkali metal, ammonium ion, phosphonium ion; R7 = alkyl, alkoxy, dialkylamino, HCO3] or MgR8Z ' [R8 = C1-6-alkyl, Ph; Z' = Cl, Br, I], in the presence of a solvent. Thus, carbonyldiazole III, was prepd. in 87% yield from imidazole, via reaction in PhCl with aq. NaOH followed by reaction with phosgene in the presence of tributylhexadecylphosphonium bromide. Keywords carbonyldiazole prepn azole salt formation condensation phosgene azolide prepn condensation phosgene Index Entries Heterocyclic compounds carbonyldiazoles; prepn. of N,N'-carbonyldiazoles from from azoles via azolide salts Heterocyclic compounds nitrogen, five-membered; prepn. of N,N'-carbonyldiazoles from from azoles via azolide salts Phase transfer catalysts Alkali metal compounds prepn. of N,N'-carbonyldiazoles from from azoles via azolide salts 57-09-0 80-73-9 1643-19-2 2751-90-8 4559-86-8 14937-45-2 108-90-7, uses 75-44-5 124-41-4 288-32-4, reactions 1073-32-1 1310-73-2, reactions 20671-53-8 40958-82-5 41253-21-8 55986-39-5 5587-42-8 530-62-1 14667-54-0 37868-93-2 41864-22-6 prepn. of N,N'-carbonyldiazoles from from azoles via azolide salts

Low-Temperature Synthesis of Tetraalkylureas from Secondary Amines and Carbon Dioxide

Low-Temperature Synthesis of Tetraalkylureas from Secondary Amines and Carbon Dioxide. Tai, Chih-Cheng; Huck, Melissa J.; McKoon, Erin P.; Woo, Tiffany; Jessop, Philip G. (Department of Chemistry, University of California-Davis, Davis, CA 95616, USA).In this article, certain chemicals are used. Some of their cas registry numbers are 124-38-9 and 4559-86-8 Journal of Organic Chemistry, 67(25), 9070-9072 (English) 2002 American Chemical Society. CODEN: JOCEAH. ISSN: 0022-3263. DOCUMENT TYPE: Journal CA Section: 23 (Aliphatic Compounds) Section cross-reference(s): 27 The reaction of dialkylamines with CO2 giving tetraalkylureas can be performed at 60°. The reaction requires CCl4, is weakly promoted by DMAN or PPh3, and is not promoted by a Pd catalyst. A two-step procedure, in which dialkylammonium dialkylcarbamate is produced in situ and then reacted with CCl4 and free dialkylamine, gave greater yields of urea than a simple single-stage procedure. .