1468-42-4Relevant articles and documents
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Schreiber,J.,Witkop,B.
, p. 2441 - 2445 (1964)
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Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation
Lan, Chunling Blue,Auclair, Karine
supporting information, p. 5135 - 5146 (2021/10/19)
Monosubstituted ureas are important scaffolds in organic chemistry. They appear in various biologically active compounds and serve as versatile precursors in synthesis. Monosubstituted ureas were originally prepared using toxic and hazardous phosgene equivalents. Modern methods include transamidation of urea and nucleophilic addition to cyanate salts, both of which suffer from a narrow substrate scope due to the need for a strong acid and prolonged reaction times. We hereby report that ammonium chloride can promote the reaction between amines and potassium cyanate to generate monosubstituted ureas in water. This method proceeds rapidly under microwave irradiation and tolerates a broad range of functional groups. Unlike previous strategies, it is compatible with other nucleophiles, acid-labile moieties, and most of the common protecting groups. The products precipitate out of solution, allowing facile isolation without column chromatography.
REACTIONS OF 6-AMINOHEXANOIC ACID WITH UREAS
Kornilina, A. N.,Zil'berman, E. N.,Spasskaya, R. I.,Matveeva, G. N.
, p. 808 - 811 (2007/10/02)
In aqueous alkaline solutions 1-alkyl-, 1,1-dialkyl-, acetyl-, and benzylureas and biuret react with 6-aminohexanoic acid, forming 6-ureidohexanoic acids.Arylureas react with 6-aminohexanoic acid with the formation of 6-(3-arylureido)hexanoic acids. 1,4-Disubstituted ureas do not react with 6-aminohexanoic acid.
Combating fungi with 1-(ω-substituted pentyl)-3-(2-cyano-acetyl)-ureas
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, (2008/06/13)
1-(ω-Substituted pentyl)-3-(2-cyano-acetyl)-ureas of the formula STR1 in which R represents R1, CO--R2, CO--NH--R3 or CO--OR4, R1 represents unsubstituted alkyl with 1 to 10 carbon atoms; or represents substituted alkyl with 1 to 4 carbon atoms, which contains, as a substituent, a vinyl group, an alkynyl group with up to 4 carbon atoms, an alkylcarbonyl group with 2 to 5 carbon atoms, an alkoxycarbonyl group with 2 to 5 carbon atoms, an alkenoxycarbonyl or alkynoxycarbonyl group with 4 to 5 carbon atoms, an aminocarbonyl group, an N-alkylaminocarbonyl or N-cycloalkylaminocarbonyl group with up to 7 carbon atoms in either case or a N-phenylaminocarbonyl group, which can optionally have C1 -C4 alkyl and/or chlorine as further substituents on the phenyl radical; or represents benzyl, which can be substituted in the aromatic part by a methyl, methoxy, methylenedioxy, nitro, trifluoromethyl, benzoyl, monochlorobenzoyl, dichlorobenzoyl, phenyl or phenoxy group or by 1 to 4 chlorine atoms; R2 represents a straight-chain or branched, saturated or unsaturated hydrocarbon radical with up to 8 carbon atoms, which can be substituted by chlorine or bromine or by a cyano group, R3 represents a straight-chain or branched alkyl radial with up to 11 carbon atoms, which can be substituted by a cyano group of by an alkoxycarbonyl radical with up to 5 carbon atoms, or represents a phenyl radical, which can be substituted y a methyl, nitro or trifluoromethyl group or by chlorine, R4 represents a saturated or unsaturated aliphatic group with up to 4 carbon atoms, Q represents CN, CO--NH2, COOH or CO--OR5, and R5 denotes an alkyl group with 1 to 4 carbon atoms, which possess fungicidal properties.
