US4297497A
Expired / Lapsed
US
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Synthesis of 2-keto-1,4-diazacycloalkanes
Assignee: Goodrich Corp
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Filing: 1979-07-13
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Granted: 1981-10-27
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Expires: 1999-07-13
Abstract
Abstract Several novel syntheses have been discovered for preparation of 2-keto-1,4-diazacycloalkanes and their derivatives. Trans isomers of polysubstituted quinoxalin-2-ones may now be prepared.
Inventors
- 👤 John T. Lai
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 00:30
CPC Classifications
C; C07; C07D; C07D241/00; C07D241/36; C07D241/38; C07D241/02; C07D241/06; C07D241/08; C07D241/40; C07D241/44; C07D243/00; C07D243/06; C07D243/08; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3462
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
75 words
A method which is directive for preparing symmetrical polysubstituted 2-keto-1,4-diazacycloalkanes, said method comprising: contacting a 1,2-diamine, a saturated monoketone and haloform in the presence of aqueous or solid alkali and a catalytic effective amount of a phase transfer catalyst of the formula R--O--R' wherein R and R' are independently selected from the group consisting of alkyl having 1 to 16 carbon atoms and substituted alkyl wherein said substituents can be hydroxy, sulfur, amine or ether.
Claim 2
Independent Claim
75 words
A method which is directive for preparing symmetrical polysubstituted 2-keto-1,4-diazacycloalkanes, said method comprising: contacting a 1,2-diamine, a saturated monoketone and haloform in the presence of aqueous or solid alkali and a catalytic effective amount of a phase transfer catalyst of the formula R--O--R' wherein R and R' are independently selected from the group consisting of alkyl having 1 to 16 carbon atoms and substituted alkyl wherein said substituents can be hydroxy, sulfur, amine or ether.
Claim 3
Dependent Claim
25 words
The method of claim 1 including, forming a polysubstituted unsaturated 2-keto-1,4-diaza cyclic compound, and hydrogenating said unsaturated cyclic compound to form said polysubstituted 2-keto-1,4-diazacycloalkane compound.
Claim 4
Dependent Claim
47 words
The method of claim 1 wherein said 1,2-diamine is selected from the group consisting of o-phenylenediamine and cyclohexyldiamine; said monoketone is selected from a cyclic ketone and an acyclic ketone; said haloform is selected from chloroform and bromoform; and, said alkali is an aqueous alkali metal hydroxide.
Claim 5
Independent Claim
53 words
The method of 1 wherein said phase transfer catalyst has the formula R--(OCH.sub.2 CH.sub.2).sub.r OR" wherein R is alkyl having from 1 to about 16 carbon atoms, R" is alkyl having from 1 to about 16 carbon atoms, or H, and r is an integer in the range from 0 to about 300.
Claim 6
Independent Claim
53 words
The method of 1 wherein said phase transfer catalyst has the formula R--(OCH.sub.2 CH.sub.2).sub.r OR" wherein R is alkyl having from 1 to about 16 carbon atoms, R" is alkyl having from 1 to about 16 carbon atoms, or H, and r is an integer in the range from 0 to about 300.
Claim 7
Dependent Claim
34 words
The method of claim 1 which comprises reacting N 1 N 3 -di-tert-butyl-2-methyl-1,2,3-propanetriamine with acetone, in the presence of (i) chloroform, (ii) sodium hydroxide and (iii) as a phase transfer catalyst, tetraethylene glycol dimethylether
References Cited (Backward Citations)
US4167512A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-10-26 | 1985-04-27 | 1985-10-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-26 | 1989-04-27 | 1989-10-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-26 | 1993-04-27 | 1993-10-27 | $7700.00 | Window Closed / Lapsed |