EP0057661A2
Expired / Lapsed
EP
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Process for the production of leuco triaryl methane compounds
Assignee: Novartis AG
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Filing: 1982-01-18
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Granted: —
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Expires: 2002-01-18
Abstract
Abstract A process for the production of a compound of formula which comprises reacting a compound of formula or a mixture of the compounds (2a) and (2b) with a compound ZH having an active hydrogen atom, 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 radical, and Z represents an aryl radical of formula wherein R i , R 2 , R 3 and R 4 , each independently of the other, represent hydrogen, hydroxy, halogen, cyano, nitro, C 1 -C 12 - alkyl, C 2 1-C 12 -alkoxy, C 2 -C 8 -alkoxyalkyl, cycloalkyl, aralkyl, aryl, aryloxy, or substituted alkyl, cycloalkyl, aralkyl or aryl, or amino or substituted amino, or a sulphonic acid group or derivates thereof, V represents oxygen, sulphur or imino and T 1 and T 2 independently represent hydrogen, C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, aryl, aralkyl, and T, is also amido or ureido, or T, and T 2 together with the nitrogen atom which links them, represent a five- or six-membered heterocyclic radical. Preferably Z contains at least one water-solubilising group, e.g. -S0 3 M, wherein M is hydrogen, ammonium or alkali metal.
Inventors
- 👤 Malcolm Colin Dr. Clark
- 👤 Derrick Alexander Hart
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 10:29
CPC Classifications
C; C09; C09B; C09B11/00; C09B11/04; C09B11/10; C09B11/24; C09B11/26
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
200 words
A process for the production of a compound of formula which comprises reacting a compound of formula or a mixture of the compounds (2a) and (2b) with a compound ZH having an active hydrogen atom, 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 radical, and Z represents an aryl radical of formula wherein R 1 , R 2 , R 3 and R 4 , each independently of the other, represent hydrogen, hydroxy, halogen, cyano, nitro, C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, C 2 -C 8 -alkoxyalkyl, cycloalkyl, aralkyl, aryl, aryloxy, or substituted alkyl, cycloalkyl, aralkyl or aryl, or amino or substituted amino, or a sulphonic acid group or a derivative thereof, V represents oxygen, sulphur or imino and T 1 and T 2 independently represent hydrogen, C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, aryl, aralkyl, and T 1 is also amido or ureido, or T 1 and T 2 together with the nitrogen atom which links them represent a five- or six-membered heterocyclic radical.
Claim 2
Dependent Claim
200 words
A process for the production of a compound of formula which comprises reacting a compound of formula or a mixture of the compounds (2a) and (2b) with a compound ZH having an active hydrogen atom, 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 radical, and Z represents an aryl radical of formula wherein R 1 , R 2 , R 3 and R 4 , each independently of the other, represent hydrogen, hydroxy, halogen, cyano, nitro, C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, C 2 -C 8 -alkoxyalkyl, cycloalkyl, aralkyl, aryl, aryloxy, or substituted alkyl, cycloalkyl, aralkyl or aryl, or amino or substituted amino, or a sulphonic acid group or a derivative thereof, V represents oxygen, sulphur or imino and T 1 and T 2 independently represent hydrogen, C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, aryl, aralkyl, and T 1 is also amido or ureido, or T 1 and T 2 together with the nitrogen atom which links them represent a five- or six-membered heterocyclic radical.
Claim 3
Dependent Claim
50 words
A process according to claim 1, wherein R 1 , R 2 , R 3 , R 4 independently represent hydrogen, hydroxy, halogen, cyano, C l -C 4 -alkyl, C 1 -C 4 - alkoxy, amino, substituted amino or -S0 3 M, wherein M is hydrogen, ammonium or alkali metal.
Claim 4
Dependent Claim
116 words
A process according to claim 1 or 2, wherein X and Y independently represent an amino- substituted phenyl radical of formula wherein R 5 and R 6 independently represent hydrogen, C 1 -C 12 alkyl, C 2 -C 8 alkoxyalkyl, cycloalkyl, aralkyl, aryl or substituted alkyl, cycloalkyl, aralkyl or aryl, or R 5 and R 6 together with the nitrogen atom which links them represent pyrrolidino, piperidino, morpholino, thiomorpholino or piperazino, and R 7 and R 8 independently represent hydrogen, hydroxy, halogen, cyano, nitro, C 1 -C 4 -alkyl, C l -C 4 -alkox y , C 2 -C 8 -alkoxyalkyl, cycloalkyl, aralkyl, aryl, aryloxy, arylamino, or a carboxylic acid, carboxylic ester or carboxylic amide group.
Claim 5
Dependent Claim
42 words
A process according to claim 3, wherein one or more of the substituents R 5 , R 6 , R 7 and R 8 contain a water-solubilising group, especially a -SO 3 M group, wherein M is hydrogen, ammonium or alkali metal.
Claim 6
Dependent Claim
46 words
A process according to claim 4, wherein R 5 and R 6 independently are hydrogen, C l -C 4 -alkyl, C 2 -C 4 -alkoxyalkyl, cyclohexyl, benzyl, phenyl, or phenyl or benzyl each substituted by -SO 3 M, wherein M is hydrogen, ammonium or alkali metal.
Claim 7
Dependent Claim
90 words
A process according to claim 1, wherein X and Y independently represent an indolyl radical of the formula wherein Q 1 represents hydrogen, C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl or benzyl, Q 2 represents hydrogen, C 1 -C 12 -alkyl or aryl, and R 7 and R 8 independently represent hydrogen, hydroxy, halogen, cyano, nitro, C l - C 4 -alkyl, C l -C 4 -alkoxy, C 2 -C 8 -alkoxyalkyl, cycloalkyl, aralkyl, aryl, aryloxy, arylamino, or a carboxylic acid, carboxylic ester or carboxylic amide group.
Claim 8
Dependent Claim
82 words
A process according to claim 1, wherein Z is a radical of formula wherein R 5 and R 6 independently represent hydrogen, C 1 -C 12 alkyl, C 2 -C 8 alkoxyalkyl, cycloalkyl, aralkyl, aryl or substituted alkyl, cycloalkyl, aralkyl or aryl, or R 5 and R 6 together with the nitrogen atom which links them represent pyrrolidino, piperidino, morpholino, thiomorpholino or piperazino, M is hydrogen, ammonium or alkali metal and R 1 and R 2 are as defined in claim 1.
Claim 9
Dependent Claim
39 words
A process according to claim 7, wherein Z is a radical of formula or wherein R 9 is alkyl or aryl, m is 1 to 4, n is 1 or 2 and M is as defined in claim 7.
Claim 10
Dependent Claim
93 words
A process according to claim 1, wherein Z is a radical of formula or wherein R' 1 is hydrogen or hydroxy, n is 1 or 2, and R and R 4 are as defined in claim 1, R 5 and R 6 independently represent hydrogen, C 1 -C 12 alkyl, C 2 -C 8 alkoxyalkyl, cycloalkyl, aralkyl, aryl or substituted alkyl, cycloalkyl, aralkyl or aryl, or R 5 and R 6 together with the nitrogen atom which links them represent pyrrolidino, piperidino, morpholino, thiomorpholino or piperazino, M is hydrogen, ammonium or alkali metal.
Claim 11
Dependent Claim
18 words
A process according to claim 8 or 9, wherein Z is a radical of formula (3a) or (6).
Claim 12
Dependent Claim
79 words
A process according to claim 1 wherein the compounds of formula (2a) and (2b) or a mixture thereof are prepared by reacting a compound of the formula wherein V, T 1 and T 2 are as defined in claim 1, under acidic conditions, with one or two molar equivalents of an aldehyde which is X-CHO or Y-CHO and one or two molar equivalent of a compound XH or YH, wherein X and Y are as defined in claim 1.
Claim 13
Dependent Claim
32 words
A process according to claim 11 wherein p-dimethylamino-benzaldehyde is reacted with urea and N,N-dimethylaniline, in the presence of an acid, to form N-14,4'-dimethylamino-diphenyl-methyl]urea or N,N'-bis[4,4'-dimethyl-amino-diphenyl-methyl]urea or a mixture of these urea derivatives.
Claim 14
Dependent Claim
146 words
A process according to claim 1, wherein a compound of formula (2a) is used, wherein each of X and Y is an aromatic carbocyclic radical having an unsubstituted or substituted amino group in the para-position, wherein this compound of formula (2a) is produced by reacting a compound of formula wherein V, T 1 and T 2 are as defined in claim 1; under acidic conditions, with a benzhydrol of formula wherein the benzene rings A and B are unsubstituted or substituted by one or more substituents selected from halogen, cyano, nitro, C l -C 4 -alkyl and C l -C 4 -alkoxy, and in which R 10 , R 11 , R 12 and R 13 each independently represent C 1 -C 12 -alkyl, cycloalkyl, aralkyl, aryl, alkoxyaryl, in which the alkoxy group has 2 to 8 carbon atoms, or substituted alkyl, cycloalkyl, aralkyl or aryl.
Claim 15
Dependent Claim
20 words
The leuco triaryl methane compound obtained according to the process as claimed in any one of claims 1 to 13.
Claim 16
Dependent Claim
32 words
The use of the leuco triaryl methane compound, obtained according to the process as claimed in any one of claims 1 to 13, as intermediate for the oxidation to produce a dyestuff.
References Cited (Backward Citations)
No citation records indexed.
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