3-Amino-acrylonitrile derivs. prepn. - by reacting salt of alkali(ne earth) metal and 3-hydroxy-acrylonitrile with amine

摘要

Prepn. of 3-aminoacrylonitriles of formula R1R2N-CH=C(R3)-CN (I). and comprises reacting an alkali metal or alkaline earth metal salt (1/alpha M)O-CH=C(R3)-CN (II) of a 3-hydroxyacrylonitrile deriv. with an amine R1R2NH (III) in the presence of a mono- or polybasic (in)organic acid, or in the presence of a salt of an inert amine. Alternatively (II) can be reacted with an amine salt of one of these acids and with the amine (III). In the formula R1 and R2 are each H, opt. branched 1-12C alkyl, alkenyl or alkynyl gps. -cyc-(CH2)n- or -X-R4; or R1 and R2 together form a 3-6 membered alkylene or alkenylene gp., opt. interrupted by =1 heteroatoms. Cys is an iso- or heterocyclic, nono- or polynuclear aromatic or cycle aliphatic ring system opt. with ring substits.; n is 0-5. X is straight chain, branched or cyclic 2-12C alkylene or alkenyl -cyc- -(CH2)n.cyc- or -(CH2)n-cyc-(CH2)n-; R4 is -N(R1)-CH=C(R3)CN; R3 is H, straight chain, branched or cyclic 1-20C alkyl opt. branched - (CH2)nCN, -(CH2)nOR or -(CH2)n-CH(OR)2. R is 1-12C alkyl or -(CH2)n+-cyc. and alpha = 1 when M is an alkali metal and alpha = 2 when M is an alkaline earth metal. (I) are used in the prepn. of heterocycles e.g. cytosine pyrinidines, isoxazoles, 5-aminopy razoles. (I) can also be used to prepare malonic acid dinitrile; aminomethylene malonic acid nitrile, herbicides and copolymers.