Process for the production of triaryl methane compounds
First Claim
1. A process for the production of a leuco compound of the formula ##STR17## which comprises the steps of preparing either an intermediate of the formula ##STR18## or a mixture of the compounds (2a) and (2b), or an intermediate of the formula ##STR19## or a mixture of compounds (2c) and (2d) by reacting under strong, non-oxidizing acidic conditions an urea derivative of the formula ##STR20## with one or two moles of an aldehyde X--CHO, Y--CHO or Z--CHO plus an equimolar amount of a compound X--H, Y--H or Z--H having an activated hydrogen atom, isolating said intermediate or mixture of intermediates, and then reacting said intermediate or mixture of intermediates with a compound of the formula Z--H or Y--H having an activated hydrogen atom under strong non-oxidizing acidic conditions, wherein Z represents an aryl radical of the formula ##STR21## and X and Y are the same or different and each represents an amino substituted phenyl radical of the formula ##STR22## or an indolyl radical of the formula ##STR23## wherein R1, R2, R3, R4 independently represent hydrogen, C1 -C4 -alkyl, C2 -C4 -alkoxyalkyl, C2 -C4 -cyanoalkyl, cyclohexyl, benzyl or phenyl, or each pair of substituents (R1 and R2) and (R3 and R4) together with the nitrogen atom to which said pair is attached represents pyrrolidino, piperidino or morpholino and R5 and R6 independently are hydrogen, halogen, methyl, methoxy or ethoxy, Q1 represents hydrogen, C1 -C12 -alkyl, C2 -C12 -alkenyl or benzyl, Q2 represents hydrogen, C1 -C12 -alkyl or phenyl, W represents hydroxy, alkoxy, phenyloxy or amino, V represents oxygen, sulphur or imino and T1 and T2 independently represent hydrogen, C1 -C12 -alkyl, C2 -C12 -alkenyl, phenyl or benzyl, or T1 and T2 together with the nitrogen atom which links them represent pyrrolidino, piperidino, pipecolino, morpholino, thiomorpholino or piperazino.
2 Assignments
0 Petitions
Accused Products
Abstract
A process for the production of a compound of formula ##STR1## which comprises reacting a compound of formula ##STR2## or a mixture of the compounds (2a) and (2b) with a compound ZH or a compound of formula ##STR3## or a mixture of the compounds (2c) and (2d) with a compound YH, both reactions under acidic conditions, wherein X and Y are the same or different and each represents an aromatic carbocyclic radical having an unsubstituted or substituted amino group in the para position to the indicated bond, or a heterocyclic group, and Z represents an aryl radical of formula ##STR4## wherein R1 and R2 independently of one another represent hydrogen, C1 -C12 alkyl, C2 -C8 -alkoxyalkyl, cycloalkyl, aralkyl, aryl, or substituted alkyl, cycloalkyl, aralkyl or aryl, or R1 and R2 together with the nitrogen atom which links them represent a five- or six-membered, preferably saturated, heterocyclic radical and
W represents hydroxy, alkoxy, aryloxy, amino or substituted amino, and the aromatic carbocyclic radical of formula (1a) or (1b) may be further substituted by one or more halogen, cyano, nitro, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,
V represents oxygen, sulphur or imino and
T1 and T2 independently represent hydrogen, C1 -C12 -alkyl, C2 -C12 -alkenyl, aryl, aralkyl, and T1 also amido or ureido, or
T1 and T2 together with the nitrogen atom which links them represent a five- or six-membered heterocyclic radical.
-
Citations
11 Claims
- 1. A process for the production of a leuco compound of the formula ##STR17## which comprises the steps of preparing either an intermediate of the formula ##STR18## or a mixture of the compounds (2a) and (2b), or an intermediate of the formula ##STR19## or a mixture of compounds (2c) and (2d) by reacting under strong, non-oxidizing acidic conditions an urea derivative of the formula ##STR20## with one or two moles of an aldehyde X--CHO, Y--CHO or Z--CHO plus an equimolar amount of a compound X--H, Y--H or Z--H having an activated hydrogen atom, isolating said intermediate or mixture of intermediates, and then reacting said intermediate or mixture of intermediates with a compound of the formula Z--H or Y--H having an activated hydrogen atom under strong non-oxidizing acidic conditions, wherein Z represents an aryl radical of the formula ##STR21## and X and Y are the same or different and each represents an amino substituted phenyl radical of the formula ##STR22## or an indolyl radical of the formula ##STR23## wherein R1, R2, R3, R4 independently represent hydrogen, C1 -C4 -alkyl, C2 -C4 -alkoxyalkyl, C2 -C4 -cyanoalkyl, cyclohexyl, benzyl or phenyl, or each pair of substituents (R1 and R2) and (R3 and R4) together with the nitrogen atom to which said pair is attached represents pyrrolidino, piperidino or morpholino and R5 and R6 independently are hydrogen, halogen, methyl, methoxy or ethoxy, Q1 represents hydrogen, C1 -C12 -alkyl, C2 -C12 -alkenyl or benzyl, Q2 represents hydrogen, C1 -C12 -alkyl or phenyl, W represents hydroxy, alkoxy, phenyloxy or amino, V represents oxygen, sulphur or imino and T1 and T2 independently represent hydrogen, C1 -C12 -alkyl, C2 -C12 -alkenyl, phenyl or benzyl, or T1 and T2 together with the nitrogen atom which links them represent pyrrolidino, piperidino, pipecolino, morpholino, thiomorpholino or piperazino.
Specification
-
- Resources
-
Current AssigneeCiba Specialty Chemicals Corp (BASF SE)
-
Original AssigneeCiba-Geigy Corporation (Novartis Ag)
-
InventorsHenshall, John B., Clark, Malcolm C., Hart, Derrick A.
-
Primary Examiner(s)Raymond, Richard L.
-
Assistant Examiner(s)Springer, D. B.
-
Application NumberUS06/597,213Time in Patent Office487 DaysField of Search548/456, 546/190, 260/390, 260/391, 544/86, 544/35.7, 544/58.7US Class Current552/106CPC Class CodesB41M 5/1366 characterised solely by tri...B41M 5/145 with a lactone or lactam ringB41M 5/323 Organic colour formers, e.g...C07C 273/1863 from ureaC07C 275/24 containing six-membered aro...C09B 11/16 Preparation from diarylketo...C09B 11/24 Phthaleins containing amino...C09B 11/26 Triarylmethane dyes in whic...
