US3883527A
Expired / Lapsed
US
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Process for preparation of 2-aryl-1,3,4-triazine-3,5(2H,4H)-diones
Assignee: Pfizer Inc
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Filing: 1973-10-19
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Granted: 1975-05-13
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Expires: 1993-10-19
Abstract
Abstract A process for making 2-aryl-1,2,4-triazine-3,5(2H,4H)-diones which comprises (a) coupling a diazotized arylamine with a lower alkyl cyanoacetate: (b) hydrolyzing and decarboxylating the lower alkyl cyanoglyoxalate arylhydrazone thus produced under alkaline conditions; and (c) cyclizing the resulting glyoxamide arylhydrazone by reaction with a dialkyl carbonate, an alkyl chloroformate or phosgene in the presence of a condensing agent to the corresponding 2-aryl-1,2,4-triazine-3,5(2H,4H)-dione. The products are useful as coccidiostats.
Inventors
- 👤 Thomas M Brennan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 13:33
CPC Classifications
C; C07; C07D; C07D253/00; C07D253/02; C07D253/06; C07D253/065; C07D253/07; C07D253/075; A; A23; A23K; A23K20/00; A23K20/10; A23K20/116; C07C; C07C251/00; C07C251/72
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
75 words
A PROCESS FOR PREPARING 2-ARYL-1,2,4- TRIAZINE3,5(2H,4H)-DIONES WHICH COMPRISES: A. COUPLING A DIAZOTIZED ARYLAMINE WITH A LOWER ALKYL CYANOACETATE TO PRODUCE A LOWER ALKYL CYANOGLYOXALATE ARYLHYDRAZONE; B. HYDROLYZING AND DECARBOXYLATING THE LOWER ALKYL CYANOGLYOXALATE ARYLHYDRAZONE THUS PRODUCED UNDER ALKALINE CONDITIONS TO PRODUCE A GLYOXAMIDE ARYLHYDRAZONE AND C. REACTING THE THUS PRODUCED GLYOXAMIDE ARYLHYDRAZONE WITH A DI(LOWER ALKYL) CARBONATE IN THE PRESENCE OF A BASIC CONDENSING AGENT TO PRODUCT A 2-ARYL-1,2,4-TRIAZINE3,5(2H,4H)-DIONE, SAID ARYLAMINE BEING OF THE FORMULA
Claim 2
Dependent Claim
75 words
A PROCESS FOR PREPARING 2-ARYL-1,2,4- TRIAZINE3,5(2H,4H)-DIONES WHICH COMPRISES: A. COUPLING A DIAZOTIZED ARYLAMINE WITH A LOWER ALKYL CYANOACETATE TO PRODUCE A LOWER ALKYL CYANOGLYOXALATE ARYLHYDRAZONE; B. HYDROLYZING AND DECARBOXYLATING THE LOWER ALKYL CYANOGLYOXALATE ARYLHYDRAZONE THUS PRODUCED UNDER ALKALINE CONDITIONS TO PRODUCE A GLYOXAMIDE ARYLHYDRAZONE AND C. REACTING THE THUS PRODUCED GLYOXAMIDE ARYLHYDRAZONE WITH A DI(LOWER ALKYL) CARBONATE IN THE PRESENCE OF A BASIC CONDENSING AGENT TO PRODUCT A 2-ARYL-1,2,4-TRIAZINE3,5(2H,4H)-DIONE, SAID ARYLAMINE BEING OF THE FORMULA
Claim 3
Dependent Claim
13 words
The process of claim 1 wherein the basic condensing agent is sodium hydride.
Claim 4
Dependent Claim
27 words
The process of claim 1 wherein each of R2 and R6 is hydrogen and each of R3, and R4 And R5 is selected from the first subgroup.
Claim 5
Dependent Claim
32 words
The process of claim 3 wherein each of R2 and R6 is hydrogen; each of R3 and R5 is selected from the first subgroup; and R4 is selected from the fourth subgroup.
Claim 6
Dependent Claim
8 words
The process of claim 4 wherein R4 is
Claim 7
Dependent Claim
8 words
The process of claim 4 wherein R4 is
Claim 8
Dependent Claim
9 words
The process of claim 5 wherein X2 is oxygen.
Claim 9
Dependent Claim
9 words
The process of claim 7 wherein R10 is -SCH3.
Claim 10
Dependent Claim
24 words
The process of claim 8 wherein R2, R6, Y2 and Y3 are each hydrogen, R3 and R5 are each methyl, and Y4 is meta-methyl.
Claim 11
Dependent Claim
10 words
The process of claim 7 wherein R10 is -SO2NR''R'' 1.
Claim 12
Dependent Claim
26 words
The process of claim 10 wherein R'', R''1, R2, and R6 are each hydrogen; R5, Y2, Y3, and Y4 are each methyl, and R3 is chloro.
Claim 13
Dependent Claim
30 words
The process of claim 10 wherein R'' is methyl, R''1 is ethyl, R2, R6, Y3, and Y4 are each hydrogen, R3 is chloro, Y2 is ortho-chloro, and R5 is methyl.
Claim 14
Dependent Claim
24 words
The process of claim 7 wherein R10 is -COCH3; R3 is chloro; R5 is methyl; R2, R6, Y2, Y3 and Y4 are each hydrogen.
Claim 15
Dependent Claim
28 words
The process of claim 10 wherein R, R5, Y2, Y3 and Y4 are each methyl, R''1 is ethyl, R3 is chloro, and R2 and R6 are each hydrogen.
Claim 16
Dependent Claim
29 words
The process of claim 10 wherein R'' and R''1 are each ethyl, R2 and R6 are each hydrogen, and R3, R5, Y2, and Y3, and Y4 are each methyl.
Claim 17
Dependent Claim
30 words
The process of claim 10 wherein R'' is hydrogen, R''1 is cyclopropyl, R2, R6, Y2, and Y3 are each hydrogen, R3 is chloro, Y4 is ortho-chloro, and R5 is methyl.
Claim 18
Dependent Claim
26 words
The process of claim 10 where R'', R2, R6, and Y4 are each hydrogen, R''1 is cyclopropyl, and R3, R5, Y2 and Y3 are each meta-methyl.
Claim 19
Dependent Claim
29 words
The process of claim 10 wherein R'' is Beta -methoxyethyl, R''1, R2, and R6 are each hydrogen, R5, Y2, Y3, and Y4 are each methyl, and R3 is chloro.
Claim 20
Dependent Claim
27 words
The process of claim 10 wherein R'' is Beta -methylthioethyl; R''1, R2, and R6 are each hydrogen; and R3, R5, Y2, Y3, and Y4 are each methyl.
Claim 21
Dependent Claim
31 words
The process of claim 10 wherein R'' is methyl; R''1 is ethyl; R3 is chloro; R5 is methyl; Y2 is ortho ethyl; and R2, R6, Y3 and Y4 is each hydrogen.
Claim 22
Dependent Claim
11 words
The process of claim 4 wherein R4 is of the formula
Claim 23
Dependent Claim
9 words
The process of claim 21 wherein X1 is -OCH2-.
Claim 24
Dependent Claim
34 words
The process of claim 22 wherein R3 is hydrogen or lower alkyl; R5 is lower alkyl or halogen; Y2 and Y3 are each hydrogen, halogen or lower alkyl; and R9 is halogen or -SO2CH3.
References Cited (Backward Citations)
US3560496A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-05-12 | 1978-11-11 | 1979-05-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-05-12 | 1982-11-11 | 1983-05-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-05-12 | 1986-11-11 | 1987-05-13 | $7700.00 | Window Closed / Lapsed |