Patent GB-1418211-A (GB)
Title: Substituted 1-arylamine-2,beta-dicyanbutanes and their use as dyestuff intermediates
IPC: C09B29/08
Filed: 1973-05-04
Abstract: 1418211 N - (2,4 - dicyanobutyl)arylamines GAF CORP 4 May 1973 [16 May 1972] 21433/73 Heading C2C [Also in Division C4] The invention comprises compounds of general Formula I wherein Ar is an aryl radical devoid of substituents in the position para to the amine substituent and R a hydrogen atom or an optionally substituted alkyl group and also the quaternary ammonium salts, cyclic amides and cyclic imides of those compounds in which R contains an amino group such as are represented by (i) general Formulae VII wherein Ar is naphthyl or a phenyl radical of Formula II wherein R 1  and R 2  are independently hydrogen C 1-7  alkyl, C 1-7  alkoxy, halogen, CF 3 , R 3 CONH or R 3 OCO wherein R 3  is C 1-7  alkyl or phenyl; R 5  is a straight or branched C 1-7  alkylene group   and -#N(R 4 ) 3  is -#N(R 4 <SP>1</SP>,R 4 <SP>11</SP>,R 4 <SP>111</SP>) in which R 4 <SP>1</SP>, B 4 <SP>11</SP> and R 4 <SP>111</SP> are independently C 1-5  alkyl   or C 7-14  aralkyl or -#N(R 4 ) 3  is a group of Formula (A) in which R 4 <SP>1111</SP> represents the residue of a heterocyclic ring and X<SP>(-)</SP> is the anion of a mineral acid, (ii) general Formula IV wherein Ar is a radical as defined in respect of Formula I; R 5  is an alkylene group; R<SP>1</SP> and R<SP>1</SP> 0  are independently H, halogen, OH, C 1-7  alkyl, chloro(C 1-7 )alkyl, bromo(C 1-7 )alkyl, hydroxy(C 1-7 )alkyl, alkoxy(C 1-7  alkyl), cyano- (C 1-7 )alkyl, carbalkoxy(C 1-7 )alkyl(C 6 -C 12 )aryl, substituted (C 6 -C 12 )aryl and C 3-8  cycloalkyl; A is selected from O, N or S; n and p are 0 or integers from 1 to 15; n + p = at least 2; z is 0 or 1 and when z is 1 Cp-R<SP>1</SP> (p-a) -A is connected through A to C n -R<SP>1</SP> 0(n-m)  thereby forming a cyclic ether, amino or thioether group; r is 0 or 1, n + p + q + r = at least 3; m and q are the number of double bonds in the Cn and Cp moieties, or when r = I, z = 0 and n = p = 1 one each of R<SP>1</SP> and R<SP>1</SP> 0  together with the carbon atom to which they are attached jointly form a C 6-12  aryl ring or a quaternary ammonium derivative of such a compound, or (iii) the general Formula V wherein Ar is as defined in respect of Formula VII; R 5  is an alkylene group; r is 0 or 1 and the group of Formula (B) represents the nucleus of a five- or six-membered cyclic amide or imide and L represents an organic radical containing not more than 1 hetero atom selected from O, S and N and being selected from substituted or unsubstituted, saturated or unsaturated radicals and the radical L is optionally substituted by halogen, OH, alkyl, chloro or bromoalkyl, hydroxyalkyl, alkoxyalkyl, cyanoalkyl, carbalkoxyalkyl, C 6-12  aryl, substituted (C 6 -C 12 ) aryl or C 3-8  cycloalkyl or a quaternary ammonium derivative of such a compound. The compounds of Formula I may be prepared (a) by reacting alphamethyleneglutaronitrile with at least one molar equivalent of an arylamine of formula ArNHR or (b) by reacting alpha-methylene glutaronitrile with an approximately molar equivalent amount of an amine of formula ArNH 2  followed by introduction of the group R by alkylation in known manner. Modification of the radical R to produce other compounds within the scope of the invention may be carried out in known manner. The compounds of Formula I have application as intermediates for the preparation of dyestuffs.