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US5360911A
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Process for the preparation of stilbazolium salts
Assignee: Molecular Optoelectronics Corp
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Filing: 1993-06-17
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Granted: 1994-11-01
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Expires: 2013-06-17
Abstract
Abstract A novel process is disclosed for producing stilbazolium salts. Said novel process employs a heterocyclic amine catalyst, such as pyrrolidine, an alkylated pyridine salt and a substituted benzaldehyde which unexpectedly results in increased reaction rates and product yields.
Inventors
- 👤 Eugene P. Boden
- 👤 Peter D. Phelps
- 👤 Kevin R. Stewart
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 18:56
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/38
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
48 words
A process for producing a stilbazolium salt by combining an alkylated pyridine salt with a substituted benzaldehyde in the presence of about 0.10 to about 0.25 equivalents of a heterocyclic amine catalyst of the formula ##STR3## wherein each R is independently a hydrogen, aliphatic, alicyclic or aromatic radical.
Claim 2
Dependent Claim
48 words
A process for producing a stilbazolium salt by combining an alkylated pyridine salt with a substituted benzaldehyde in the presence of about 0.10 to about 0.25 equivalents of a heterocyclic amine catalyst of the formula ##STR3## wherein each R is independently a hydrogen, aliphatic, alicyclic or aromatic radical.
Claim 3
Dependent Claim
77 words
A process for producing a stilbazolium salt comprising the steps of: (a) combining an alkylated pyridine salt and a substituted benzaldehyde to produce a salt stock solution; (b) adding to said salt stock solution about 0.10 to about 0.25 equivalents of a heterocyclic amine catalyst of the formula ##STR4## wherein each R is independently a hydrogen, aliphatic, alicyclic or aromatic radical; (c) allowing said stilbazolium salt to precipitate; (d) recovering said stilbazolium salt in substantially pure form.
Claim 4
Dependent Claim
77 words
A process for producing a stilbazolium salt comprising the steps of: (a) combining an alkylated pyridine salt and a substituted benzaldehyde to produce a salt stock solution; (b) adding to said salt stock solution about 0.10 to about 0.25 equivalents of a heterocyclic amine catalyst of the formula ##STR4## wherein each R is independently a hydrogen, aliphatic, alicyclic or aromatic radical; (c) allowing said stilbazolium salt to precipitate; (d) recovering said stilbazolium salt in substantially pure form.
Claim 5
Dependent Claim
18 words
A process in accordance with claim 2 wherein said heterocyclic amine catalyst is represented by the formula ##STR5##
Claim 6
Dependent Claim
14 words
A process in accordance with claim 2 wherein said stilbazolium salt is 4'-dimethylamino-N-methylstilbazolium p-toluenesulfonate.
Claim 7
Dependent Claim
14 words
A process in accordance with claim 2 wherein said stilbazolium salt is 4-dimethylamino-N-methylstilbazolium methanesulfonate.
Claim 8
Dependent Claim
14 words
A process in accordance with claim 2 wherein said stilbazolium salt is 4-methoxy-N-methylstilbazolium p-toluenesulfonate.
Claim 9
Dependent Claim
16 words
A process in accordance with claim 2 wherein said alkylated pyridine salt is a picoline salt.
Claim 10
Dependent Claim
20 words
A process in accordance with claim 7 wherein said picoline salt is prepared from 4-picoline and an organic sulfonate ester.
Claim 11
Dependent Claim
17 words
A process in accordance with claim 8 wherein said organic sulfonate ester is methanesulfonate or methyl p-toluenesulfonate.
Claim 12
Dependent Claim
15 words
A process in accordance with claim 2 wherein said salt stock solution comprises a solvent.
Claim 13
Dependent Claim
14 words
A process in accordance with claim 10 wherein said solvent is an aliphatic alcohol.
Claim 14
Dependent Claim
16 words
A process in accordance with claim 11 wherein said aliphatic alcohol is methanol, ethanol or propanol.
Claim 15
Dependent Claim
15 words
A process in accordance with claim 2 wherein said substituted benzaldehyde is dimethylaminobenzaldehyde or p-methoxybenzaldehyde.
Claim 16
Dependent Claim
25 words
A process in accordance with claim 2 wherein about 0.10 to about 0.15 equivalents of heterocyclic amine catalyst is added to said salt stock solution.
Claim 17
Dependent Claim
15 words
A process in accordance with claim 2 wherein said stilbazolium salt is recovered by filtration.
Claim 18
Dependent Claim
20 words
A process in accordance with claim 1 wherein about 0.10 to about 0.15 equivalents of heterocyclic amine catalyst are present.
Claim 19
Dependent Claim
19 words
A process in accordance with claim 1 wherein said substantially pure stilbazolium salt is at least about 95% pure.
Claim 20
Dependent Claim
17 words
A process in accordance with claim 2 wherein said stilbazolium salt is a substantially pure stilbazolium salt.
Claim 21
Dependent Claim
19 words
A process in accordance with claim 18 wherein said substantially pure stilbazolium salt is at least about 95% pure.
References Cited (Backward Citations)
US3085935A
Cited
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