Patent GB-923734-A (GB)
Title: Improvements relating to substituted pyrazoles
Inventor: DICKINSON CLIFFORD LEE JR
IPC: C07D231/38
Filed: 1959-06-16
Abstract: Condensation polymers are obtained by (i) reacting a diol or a diprimary diamine with the dicarboxylic acids obtained by the hydrolysis of compounds of formula <FORM:0923734/IV(a)/1> where one of X and Y is cyano and the other is a group -NR1R2, where R1 is hydrogen or acyl and R2 is hydrogen or R1 and R2 together form a hydrocarbyl or substituted hydrocarbyl radical doubly bonded to the nitrogen atom by a C=N bond, and R is hydrogen, hydrocarbyl, substituted hydrocarbyl or acyl (which term includes carboxylic acyl, sulphonyl, carbonyl and substituted carbonyl) (see Group IV(b)); and (ii) reacting a dibasic acid such as adipic acid with the di(amino methyl) compounds obtained by the reduction of the compounds of the above formula.  Specification 757,773 is referred to.ALSO:The invention comprises compounds of the formula <FORM:0923734/IV(a)/1> where one of X and Y is cyano and the other is a group -NR1R2 where R1 is hydrogen or acyl and R2 is hydrogen, or R1 and R2 together form a hydrocarbyl or substituted hydrocarbyl radical doubly bonded to the nitrogen atom by a C = N bond, and R is hydrogen, hydrocarbyl, substituted hydrocarbyl or acyl; "acyl" comprises carboxylic acyl, sulphonyl, carbamyl and substituted carbamyl.  Compounds in which R1 and R2 are both hydrogen are prepared by reacting tetracyanoethylene with a substituted hydrazine RNHNH2 in a molar ratio between 1:1.5 and 1.5:1.  Compounds in which R1 is acyl are prepared by acylating the free amino compound; the ring nitrogen may be acylated at the same time.  The compounds in which R1 and R2 are together a single radical are prepared by reacting the free amino compounds with an aldehyde or ketone.  Compounds in which R is hydrogen may be prepared by hydrolysis of compounds in which R is acyl, especially carbamyl. The compounds of the invention may be further treated as follows:-(i) the cyano groups may be hydrolysed to carboxylic acid groups, (ii) the cyano groups may be reduced to aminomethyl groups, and (iii) the imino compounds may be reduced to amino compounds. 4-n-Butyl-4-stearyl semicarbazide is obtained by reacting hydrazine with N-n-butyl-N-stearyl carbamyl chloride, itself obtained from N-n-butyl stearylamine and phosgene.  4-Diethyleneoxy-semicarbazide is obtained by reacting hydrazine with the condensation product obtained from morpholine and phosgene.  Specification 757,773 is referred to.ALSO:Dyestuffs of formula <FORM:0923734/IV(a)/1> where one of X and Y is cyano and the other is a group NR1R2, where R1 and R2 together form a hydrocarbyl or substituted hydrocarbyl radical doubly bonded to the nitrogen atom by a C=N bond, and R is hydrogen, hydrocarbyl, substituted hydrocarbyl or acyl (which term includes carboxylic acyl, sulphonyl, carbamyl and substituted carbamyl) are obtained by reacting an aldehyde or ketone with the corresponding free amine.  Examples prepare and use <FORM:0923734/IV(a)/2> and the corresponding compound containing phenyl attached to the ring nitrogen instead of -CONH2.  Other aldehydes and ketones specified are butyraldehyde, benzaldehyde, naphthaldehyde and cyclohexanone. Specification 757,773 is referred to.