Isocyanic acid reaction with amines

A convenient method for the synthesis and derivatization of enantiopure a-iso-cyanato carboxylic acid esters starting from a-amino acid esters has been devised [314], The isocyanates are obtained in enantiomerically pure form (> 99% ee) by a DMAP-catalyzed isocyanation with B0C2O, which proceeds in 10 min at room temperature (for typical procedures employing B0C2O, see the B0C2O Section of the present chapter). In situ derivatization of the isocyanates by reaction with amines and alcohols affords the corresponding enantiopure ureas and carbamates. Methyl esters of various amino acids 472 have been carbonylated by B0C2O at ambient temperature [314]. 

Other experimental reproductive effects. A skin and severe eye irritant. A narcotic. Human mutation data reported. A common air contaminant. Highly flammable liquid. NCxmres of 30-60% of the vapor in air ignite above 100°. It can react violently with acid anhydrides, alcohols, ketones, phenols, NH3, HCN, H2S, halogens, P, isocyanates, strong alkalies, and amines. Reactions with cobalt chloride, mercury(II) chlorate, or mercury(II) perchlorate form violendy in the presence of traces of metals or acids. Reaction with oxygen may lead to detonation. When heated to decomposition it emits acrid smoke and fumes. 

AMINOBENZENESULFONIC ACID or p-AMINOBENZENESULFONIC ACID (121-57-3) CsH NOjS HjO Decomposes on contact with strong acids, forming sulfur trioxide. The aqueous solution is acidic reaction with strong bases. Incompatible with alkylene oxides, aliphatic amines, alkanolamines, amides, ammonia, epichlorohydrin, organic anhydrides, isocyanates, oxidizers, vinyl acetate. On small fires, use dry chemical powder (such as Purple-K-Powder), Halon , water spray, or CO2 extinguishers. 

CjHyNOjS HjO Decomposes on contact with strong acids, forming sulfur trioxide. The aqueous solution is acidic reaction with strong bases. Incompatible with alkylene oxides, aliphatic amines, aUcanolamines, amides, ammonia, epichlorohydrin, organic anhydrides, isocyanates. 

CAPRYLIC ACID or -CAPRYLIC ACID ( 1 24-07-2) CgHjsOi CH3(CH2)jCOOH Forms explosive mixture with air (flash point 230°F/110°C). Violent reaction with amines, strong oxidizers, fiirfuryl alcohol (explosion), hypochlorites, isocyanides, nitromethane, chromic acid, nitric acid, hydrogen peroxide, phosphorus pentaoxide, all bases (exothermic reaction) sulfuric acid. Reacts with azo/diazo compounds, dithiocarbamates, dithionites (forming sulfur dioxide) isocyanates, mercaptans, nitrides, nitrates, sulfides. 

---