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US3985749A
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US
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Process for preparation of 4-aminoquinazoline
Assignee: Eastman Kodak Co
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Filing: 1975-12-22
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Granted: 1976-10-12
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Expires: 1995-12-22
Abstract
Abstract Process for preparation of a 4-aminoquinazoline which comprises the steps of 1. reacting an isatoic anhydride with an equimolar amount of ammonia in the presence of dimethyl formamide, the weight of dimethyl formamide to isatoic anhydride being from about 1:1 to about 10:1; 2. adding to the solution from about 1 to about 2 mole proportions of phosphorous oxychloride based on the amount of isatoic anhydride while maintaining the solution at a temperature of from about -10° to about 15°C.; 3. increasing the temperature of the solution to about 40° to about 55°C. and maintaining the solution in this temperature range for at least 20 minutes; 4. adding sufficient water to hydrolyze an excess phosphorous oxychloride; any 5. adding to the reaction mixture at least one mole proportion based on the amount of isatoic anhydride in step (1) of an amine and sufficient base to render the mixture neutral or basic; 6. heating the reaction mixture at a temperature from about 70° to about 100°C. for at least about 15 minutes; and 7. recovering the 4-aminoquinazoline; These compounds are biologically active and useful, for example, in treating coccidiosis in poultry.
Inventors
- 👤 Charles H. Foster
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 22:00
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/70; C07D239/72; C07D239/86; C07D239/94
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
223 words
Process for preparation of a 4-aminoquinazoline having the formula ##SPC6## which comprises the steps of 1. reacting an isatoic anhydride having the formula ##SPC7## with an equimolar amount of ammonia in the presence of dimethyl formamide, the weight of dimethyl formamide to isatoic anhydride being from about 1:1 to about 10:1; 2. adding to the solution from about 1 to about 2 mole proportions of phosphorous oxychloride based on the amount of isatoic anhydride while maintaining the solution at a temperature of from about -10° to about 15° C.; 3. increasing the temperature of the solution to about 40° to about 55° C. and maintaining the solution in this temperature range for at least 20 minutes; 4. adding sufficient water to hydrolyze any excess phosphorous oxychloride; 5. adding to the reaction mixture at least one mole proportion based on the amount of isatoic anhydride in step (1) of an amine having the formula R--NH 2 and sufficient base to render the mixture neutral or basic; 6. heating the reaction mixture at a temperature from about 70° to about 100° C. for at least about 15 minutes; and 7. recovering the 4-aminoquinazoline; wherein each X is the same or different and represents hydrogen, chloro, bromo or iodo; and R is hydrogen, alkyl having 1 to about 6 carbon atoms, benzyl, phenyl, m-tolyl or p-tolyl.
Claim 2
Dependent Claim
223 words
Process for preparation of a 4-aminoquinazoline having the formula ##SPC6## which comprises the steps of 1. reacting an isatoic anhydride having the formula ##SPC7## with an equimolar amount of ammonia in the presence of dimethyl formamide, the weight of dimethyl formamide to isatoic anhydride being from about 1:1 to about 10:1; 2. adding to the solution from about 1 to about 2 mole proportions of phosphorous oxychloride based on the amount of isatoic anhydride while maintaining the solution at a temperature of from about -10° to about 15° C.; 3. increasing the temperature of the solution to about 40° to about 55° C. and maintaining the solution in this temperature range for at least 20 minutes; 4. adding sufficient water to hydrolyze any excess phosphorous oxychloride; 5. adding to the reaction mixture at least one mole proportion based on the amount of isatoic anhydride in step (1) of an amine having the formula R--NH 2 and sufficient base to render the mixture neutral or basic; 6. heating the reaction mixture at a temperature from about 70° to about 100° C. for at least about 15 minutes; and 7. recovering the 4-aminoquinazoline; wherein each X is the same or different and represents hydrogen, chloro, bromo or iodo; and R is hydrogen, alkyl having 1 to about 6 carbon atoms, benzyl, phenyl, m-tolyl or p-tolyl.
Claim 3
Dependent Claim
18 words
The process of claim 1 wherein X is hydrogen or chloro and R is hydrogen, methyl or phenyl.
Claim 4
Dependent Claim
202 words
Process for preparation of a 4-aminoquinazoline having the formula ##SPC8## which comprises the steps of 1. reacting an anthranilamide having the formula ##SPC9## with from 1 to about 2 mole proportions of phosphorous oxychloride in the presence of dimethyl formamide, the weight of dimethyl formamide to anthranilamide being from about 1:1 to about 10:1 while maintaining the solution at a temperature of from about -10° to about 15° C.; 2. increasing the temperature of the solution to about 40° to about 55° C. and maintaining the solution in this temperature range for at least 20 minutes; 3. adding sufficient water to hydrolyze any excess phosphorous oxychloride; 4. adding to the reaction mixture at least one mole proportion based on the amount of anthranilamide in step (1) of an amine having the formula R--NH 2 and sufficient base to render the mixture neutral or basic; 5. heating the reaction mixture at a temperature from about 70° to about 100° C. for at least about 15 minutes; and 6. recovering the 4-aminoquinazoline; wherein each X is the same or different and represents hydrogen, chloro, bromo or iodo; and R is hydrogen, alkyl having 1 to about 6 carbon atoms, benzyl, phenyl, m-tolyl or p-tolyl.
Claim 5
Dependent Claim
202 words
Process for preparation of a 4-aminoquinazoline having the formula ##SPC8## which comprises the steps of 1. reacting an anthranilamide having the formula ##SPC9## with from 1 to about 2 mole proportions of phosphorous oxychloride in the presence of dimethyl formamide, the weight of dimethyl formamide to anthranilamide being from about 1:1 to about 10:1 while maintaining the solution at a temperature of from about -10° to about 15° C.; 2. increasing the temperature of the solution to about 40° to about 55° C. and maintaining the solution in this temperature range for at least 20 minutes; 3. adding sufficient water to hydrolyze any excess phosphorous oxychloride; 4. adding to the reaction mixture at least one mole proportion based on the amount of anthranilamide in step (1) of an amine having the formula R--NH 2 and sufficient base to render the mixture neutral or basic; 5. heating the reaction mixture at a temperature from about 70° to about 100° C. for at least about 15 minutes; and 6. recovering the 4-aminoquinazoline; wherein each X is the same or different and represents hydrogen, chloro, bromo or iodo; and R is hydrogen, alkyl having 1 to about 6 carbon atoms, benzyl, phenyl, m-tolyl or p-tolyl.
Claim 6
Dependent Claim
18 words
The process of claim 3 wherein X is hydrogen or chloro and R is hydrogen, methyl or phenyl.
References Cited (Backward Citations)
US3541094A
Cited
US3560619A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-10-12 | 1980-04-12 | 1980-10-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-10-12 | 1984-04-12 | 1984-10-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-10-12 | 1988-04-12 | 1988-10-12 | $7700.00 | Window Closed / Lapsed |