US4125727A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Method of preparing imidazoisoindolediones
Assignee: Wyeth Holdings LLC
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Filing: 1977-07-25
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Granted: 1978-11-14
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Expires: 1997-07-25
Abstract
Abstract The invention is a novel method for preparing imidazoisoindolediones which are useful herbicidal agents.
Inventors
- 👤 Marinus Los
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 23:15
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
152 words
A method for the preparation of a compound having the formula: ##STR60## wherein X is H, CH 3 , NO 2 , Cl, OCH 3 or SCH 3 ; R 1 is alkyl C 1 -C 4 and R 2 is alkyl C 1 -C 6 , cycloalkyl C 3 -C 6 , alkenyl C 2 -C 4 , phenyl, halophenyl or benzyl; and when R 1 and R 2 are taken together they may form cycloalkyl C 3 -C 6 optionally substituted with methyl, comprising; heating a compound having the structure: ##STR61## wherein X, R 1 and R 2 are as described to a temperature between about 80° C. and 150° C. in the presence of an inert organic solvent and a reagent of alkali metal hydrides or alkali metal hydroxides and removing any water formed during cyclization of the above-identified phthalimidocarboxamide from the reaction mixture and obtaining the above-identified imidazoisoindoledione.
Claim 2
Independent Claim
152 words
A method for the preparation of a compound having the formula: ##STR60## wherein X is H, CH 3 , NO 2 , Cl, OCH 3 or SCH 3 ; R 1 is alkyl C 1 -C 4 and R 2 is alkyl C 1 -C 6 , cycloalkyl C 3 -C 6 , alkenyl C 2 -C 4 , phenyl, halophenyl or benzyl; and when R 1 and R 2 are taken together they may form cycloalkyl C 3 -C 6 optionally substituted with methyl, comprising; heating a compound having the structure: ##STR61## wherein X, R 1 and R 2 are as described to a temperature between about 80° C. and 150° C. in the presence of an inert organic solvent and a reagent of alkali metal hydrides or alkali metal hydroxides and removing any water formed during cyclization of the above-identified phthalimidocarboxamide from the reaction mixture and obtaining the above-identified imidazoisoindoledione.
Claim 3
Dependent Claim
22 words
A method according to claim 1 wherein the alkali metal hydride is sodium hydride and the solvent is toluene, benzene or xylenes.
Claim 4
Dependent Claim
22 words
A method according to claim 1 wherein the alkali metal hydroxide is sodium hydroxide and the solvent is toluene, benzene or xylenes.
Claim 5
Independent Claim
139 words
A method for the preparatin of a compound having the formula: ##STR62## wherein X is H, CH 3 , NO 2 , Cl, OCH 3 or SCH 3 ; R 1 is alkyl C 1 -C 4; and R 2 is alkyl C 1 -C 6 , cycloalkyl C 3 -C 6 , alkenyl C 2 -C 4 , phenyl, halophenyl or benzyl; and when R 1 and R 2 are taken together with the carbon to which they are attached, they may form cycloalkyl C 3 -C 6 optionally substituted with methyl; comprising heating a compound having the formula: ##STR63## wherein X, R 1 and R 2 are as defined, with an alkali metal hydride at a temperature between 80° C. and 150° C. in the presence of an inert organic solvent until the aboveidentified imidazoisoindoledione is formed.
Claim 6
Independent Claim
139 words
A method for the preparatin of a compound having the formula: ##STR62## wherein X is H, CH 3 , NO 2 , Cl, OCH 3 or SCH 3 ; R 1 is alkyl C 1 -C 4; and R 2 is alkyl C 1 -C 6 , cycloalkyl C 3 -C 6 , alkenyl C 2 -C 4 , phenyl, halophenyl or benzyl; and when R 1 and R 2 are taken together with the carbon to which they are attached, they may form cycloalkyl C 3 -C 6 optionally substituted with methyl; comprising heating a compound having the formula: ##STR63## wherein X, R 1 and R 2 are as defined, with an alkali metal hydride at a temperature between 80° C. and 150° C. in the presence of an inert organic solvent until the aboveidentified imidazoisoindoledione is formed.
Claim 7
Dependent Claim
22 words
A method according to claim 4 wherein the alkali metal hydride is sodium hydride and the solvent is toluene, benzene or xylenes.
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-11-13 | 1982-05-15 | 1982-11-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-13 | 1986-05-15 | 1986-11-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-13 | 1990-05-15 | 1990-11-14 | $7700.00 | Window Closed / Lapsed |