Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-02-04
1995-01-10
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
562844, 562859, 562862, C07B 4108, C07D21106, C07C26906
Patent
active
053808550
ABSTRACT:
A process for preparing N,N-substituted carbamoyl halides comprising (a) contacting carbon dioxide and a secondary amine in the presence of an aprotic organic solvent and a base selected from the group consisting of a phosphazene compound, an organic, nitrogenous base, mixtures of pyridine and a phosphazene compound or an organic, nitrogenous base, and mixtures thereof, to produce the corresponding ammonium carbamate salt, and (b) reacting the ammonium carbamate salt with a halide-containing electrophilic compound to produce the corresponding N,N-substituted carbamoyl halides. A second embodiment comprises recovering the ammonium carbamate salt of step (a) prior to reacting the ammonium carbamate salt with an halide-containing electrophilic compound in the presence of an aprotic organic solvent and a base selected from the group consisting of a phosphazene compound, an organic, nitrogenous base, mixtures of pyridine and a phosphazene compound or an organic, nitrogenous base, and mixtures thereof.
REFERENCES:
patent: 4467089 (1984-08-01), Bechara
patent: 4542214 (1985-09-01), Bechara
patent: 5055577 (1991-10-01), Riley et al.
patent: 5189205 (1993-02-01), McGhee et al.
patent: 5223638 (1993-06-01), McGhee et al.
Hoshino, et al., "A Convenient Preparation of Certain N,N-Dialkylcarbamoyl Chlorides", Synthetic Communications., 17(16), pp. 1887-1892 (1987).
Boger, et al., "Activation and Coupling of Pyrrole-1-carboxylic Acid in the Formation of Pyrrole N-Carbonyl Compounds: Pyrrole-1-carboxylic Acid Anhydride", J. Org. Chem., vol. 52, No. 11, 1987, pp. 2319-2323.
Bruneau et al., "Catalytic Synthesis of O-.beta.-Oxoalkylcarbamates", Tetrahedron Letters, vol. 28, No. 18, pp. 2005-2008 (1987).
McGhee et al., "Palladium-Catalyzed Generation of O-Allylic Urethanes and Carbonates from Amines/Alcohols, Carbon Dioxide and Allylic Chlorides", Organometallics, vol. 12, No. 4, pp. 1429-1433 (1993).
Shim et al., "Synthesis of Carbamates from Amine, Acetylenic Alcohol, and CO.sub.2 using Lanthanide as Catalysts", Bull. Korean Chem. Soc., vol. 11, No. 5, pp. 467-468, (1990).
Kirk-Othmer Encyclopedia of Chemical Technology, "Friedel-Crafts Reactions", vol. 11, Third Edition, p. 286, (1982).
Kirk-Othmer Encyclopedia of Chemical Technology, "Herbicides", vol. 12, Third Edition, pp. 324-325, (1982).
March, Advanced Organic Chemistry, Third Edition, pp. 388-389, (1985).
McGhee William D.
Talley John J.
Bolding James C.
Goetz Kenneth D.
Hydorn Michael B.
Monsanto Company
Passley Paul L.
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