N-Cyanoimidates, their preparation and rearrangement to pyrimidines.

摘要

Propenimidates are provided having the formula: <CHEM> Wherein X and Y are independently O or S; and R<1> and R<2> are independently C1-C4 alkyl, (CH2)nOR<3> where R<3> is C1-C4 alkyl and n is 1 or 2, CH2CH2Cl, or CH2CF3, provided that when R<1> or R<2> is CH2CH2Cl or CH2CF3, then the respective X or Y is O. Preferred propenimidates have X and Y as O and R<1> and R<2> as methyl or ethyl. The propenimidates are made either by preparing a monohydrohalide salt from a dihydrohalide salt of the formula: <CHEM> and then contacting the monohydrohalide salt with cyanamide or by contacting the dihydrohalide salt with two equivalents of a base to produce a bisimidate; contacting the bisimidate with cyanogen chloride to produce a mixture of N-cyanoimidate and a monohydrohalide bisimidate salt; and isolating the N-cyanoimidate. The propenimidates upon heating ring close to pyrimidines which are useful in preparing herbicidal compounds.