Abstract
The reactions of n-alkyl halides and potassium cyanate with primary alcohols in dimethylformamide as a solvent were systematically studied to give n-alkyl N-n-alkyl carbamates and tri-n-alkyl isocyanurates. The molar ratio of the resulting carbamate to the isocyanurate increases with the amount of primary alcohol added, and the use of more than 4.0 moles of primary alcohol per mole of n-alkyl halide yields only carbamate. The increase of carbon numbers (C4-C8) which are contained in primary alkanol or n-alkyl halide does not exert an appreciable influence on the molar ratio of the two products mentioned above. That is, in the use of 1.5 moles of primary alkanol per mole of n-alkyl halide, the resulting carbamates are almost constantly obtained at the ratio of about six moles per mole of the corresponding isocyanurates. But the use of allyl halide instead of n-alkyl halide in the reaction with the presence of primary alkanol reduces the molar ratio by about a half, and in the case of n-alkyl halide and allyl alcohol, the molar ratio increases about one and a half. The physical properties of the N-substituted urethans including several new compounds and tri-n-alkyl and tri-allyl isocyanurates preparations were examined.
