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US4065459A
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Process for the preparation of thieno(3,2-c) pyridine and derivatives thereof
Assignee: Parcor SARL
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Filing: 1976-02-06
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Granted: 1977-12-27
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Expires: 1996-02-06
Abstract
Abstract This invention relates to a process for the preparation of compounds having the formula: <IMAGE> (I) in which R1 is H or lower alkyl and R2 is H or lower alkyl, or phenyl or benzyl optionally substituted with at least one halogen or a lower alkyl, lower alkoxy, trifluoromethyl or nitro group.
Inventors
- 👤 Alan Heymes
- 👤 Jean-Pierre Maffrand
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 20:13
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; A; A61; A61P; A61P31/00; A61P31/04; C07D501/00; C07D501/14; C07D501/16; C07D501/20
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
223 words
Process for the preparation of compounds having the formula: ##STR7## in which R 1 is selected from the group consisting of hydrogen and the alkyl groups having 1-6 carbon atoms and R 2 is selected from the group consisting of hydrogen and the lower alkyl groups having 1-6 carbon atoms, comprising reacting at room temperature in methylene chloride or chloroform as a solvent and in the presence of a hydrohalic acid binding agent, a compound of the formula (II): ##STR8## in which the radicals R 1 and R 2 having the above-defined meanings and R 3 is selected from the group consisting of hydrogen, an alkyl group, a substituted alkyl group, a benzyl radical and a substituted benzyl radical, with a halosulfonated derivative of the formula: Hal -- SO.sub.2 -- R (III) in which Hal represents halogen and R is selected from the group consisting of the alkyl groups, the substituted alkyl groups, the aryl groups, the substituted aryl groups, the aralkyl groups and the substituted aralkyl groups, to give a N-substituted derivative having the formula: ##STR9## in which the various symbols having the above-defined meanings and heating the sulfonated derivative of the formula (IV) in an organic solvent selected from dioxane and the lower alkanols at refluxing temperature in the presence of an acid, to give the compound of the formula (I).
Claim 2
Dependent Claim
223 words
Process for the preparation of compounds having the formula: ##STR7## in which R 1 is selected from the group consisting of hydrogen and the alkyl groups having 1-6 carbon atoms and R 2 is selected from the group consisting of hydrogen and the lower alkyl groups having 1-6 carbon atoms, comprising reacting at room temperature in methylene chloride or chloroform as a solvent and in the presence of a hydrohalic acid binding agent, a compound of the formula (II): ##STR8## in which the radicals R 1 and R 2 having the above-defined meanings and R 3 is selected from the group consisting of hydrogen, an alkyl group, a substituted alkyl group, a benzyl radical and a substituted benzyl radical, with a halosulfonated derivative of the formula: Hal -- SO.sub.2 -- R (III) in which Hal represents halogen and R is selected from the group consisting of the alkyl groups, the substituted alkyl groups, the aryl groups, the substituted aryl groups, the aralkyl groups and the substituted aralkyl groups, to give a N-substituted derivative having the formula: ##STR9## in which the various symbols having the above-defined meanings and heating the sulfonated derivative of the formula (IV) in an organic solvent selected from dioxane and the lower alkanols at refluxing temperature in the presence of an acid, to give the compound of the formula (I).
Claim 3
Dependent Claim
17 words
Process as claimed in claim 1, wherein the hydrohalic acid binding agent is an alkali metal carbonate.
Claim 4
Dependent Claim
14 words
Process as claimed in claim 2, wherein said alkali metal carbonate is potassium carbonate.
Claim 5
Dependent Claim
20 words
Process as claimed in claim 1, wherein said lower alkanol is selected from the group consisting of ethanol and propanol.
Claim 6
Dependent Claim
14 words
Process as claimed in claim 1, wherein said acid is a strong mineral acid.
Claim 7
Dependent Claim
21 words
Process as claimed in claim 5, wherein said acid is selectd from the group consisting of hydrochloric acid and hydrobromic acid.
References Cited (Backward Citations)
US3969358A
Cited
US3983125A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-26 | 1981-06-27 | 1981-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-26 | 1985-06-27 | 1985-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-26 | 1989-06-27 | 1989-12-27 | $7700.00 | Window Closed / Lapsed |