US4175188A
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Process for the production of 1,2,4-triazin-5-one derivatives
Assignee: Evonik Operations GmbH
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Filing: 1978-07-12
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Granted: 1979-11-20
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Expires: 1998-07-12
Abstract
Abstract 1,2,4-triazin-5-one compounds of the general formula (I) ##STR1## where R is ##STR2## are prepared by reacting a compound of general formula (II) ##STR3## in which R is defined above with either (a) a tertiary alcohol of general formula (III) HO--R' (III) in which R' is a t-alkyl group having 4 to 18 carbon atoms, especially t-amyl or t-octyl or preferably t-butyl or (b) an alkene of general formula (IV) ##STR4## in which R 1 and R 2 are the same or different and are hydrogen or an alkyl group and R 3 and R 4 are the same or different and wherein the alkyl groups in each case can be 1 to 15 carbon atoms and wherein preferably R 1 and R 2 are hydrogen and R 3 and R 4 each are methyl to form an α-ketocarboxylic acid amide of general formula (V) ##STR5## and this, in a given case after previous saponification to the free acid, condensed with thiocarbohydrazide ##STR6## to form a 1,2,4-triazin-5-one compound of general formula (VI) ##STR7## and then the mercapto group is methylated.
Inventors
- 👤 Herbert Klenk
- 👤 Werner Schwarze
- 👤 Wolfgang Leuchtenberger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 06:53
CPC Classifications
C; C07; C07D; C07D253/00; C07D253/02; C07D253/06; C07D253/065; C07D253/07; C07D253/075; A; A01; A01N; A01N43/00; A01N43/64; A01N43/707
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
137 words
A process for the production of a 1,2,4-triazin-5-one compound of the formula ##STR20## where R is ##STR21## are prepared by reacting under acid conditions an acyl cyanide of the formula ##STR22## with either (a) a tertiary alcohol of the formula H--O--R' (III) in which R' is a t-alkyl group having 4 to 18 carbon atoms or (b) an alkene of the formula ##STR23## where R 1 and R 2 are hydrogen or alkyl and R 3 and R 4 are alkyl of 1 to 15 carbon atoms to form an α-ketocarboxylic acid amide of the formula ##STR24## and then either (1) reacting compound (V) with thiocarbohydrazide or (2) saponifying (V) to the free carboxylic acid and condensing the free carboxylic acid with thiocarbohydrazide to form a 1,2,4-triazin-5-one of the formula ##STR25## and then methylating the mercapto group.
Claim 2
Dependent Claim
137 words
A process for the production of a 1,2,4-triazin-5-one compound of the formula ##STR20## where R is ##STR21## are prepared by reacting under acid conditions an acyl cyanide of the formula ##STR22## with either (a) a tertiary alcohol of the formula H--O--R' (III) in which R' is a t-alkyl group having 4 to 18 carbon atoms or (b) an alkene of the formula ##STR23## where R 1 and R 2 are hydrogen or alkyl and R 3 and R 4 are alkyl of 1 to 15 carbon atoms to form an α-ketocarboxylic acid amide of the formula ##STR24## and then either (1) reacting compound (V) with thiocarbohydrazide or (2) saponifying (V) to the free carboxylic acid and condensing the free carboxylic acid with thiocarbohydrazide to form a 1,2,4-triazin-5-one of the formula ##STR25## and then methylating the mercapto group.
Claim 3
Dependent Claim
10 words
A process according to claim 1 which includes step (1).
Claim 4
Dependent Claim
9 words
A process according to claim 2 including compound (a).
Claim 5
Dependent Claim
13 words
A process according to claim 3 wherein R' is t-amyl, t-octyl or t-butyl.
Claim 6
Dependent Claim
10 words
A process according to claim 4 wherein R' is t-butyl.
Claim 7
Dependent Claim
22 words
A process according to claim 3 wherein there is employed 1.5 to 2 moles of compound (III) per mole of acyl cyanide.
Claim 8
Dependent Claim
21 words
A process according to claim 3 wherein there are used 1 to 10 moles of acid per mole of acyl cyanide.
Claim 9
Dependent Claim
17 words
A process according to claim 7 wherein the acid is sulfuric acid or an organic sulfonic acid.
Claim 10
Dependent Claim
21 words
A process according to claim 8 wherein there are used 1.1 to 1.5 moles of acid per mole of acyl cyanide.
Claim 11
Dependent Claim
22 words
A process according to claim 9 wherein there are employed 1.5 to 2 moles of compound (III) per mole of acyl cyanide.
Claim 12
Dependent Claim
18 words
A process according to claim 8 wherein the methylating agent is methyl bromide, methyl iodide or dimethyl sulfate.
Claim 13
Dependent Claim
10 words
A process according to claim 2 wherein R is t-butyl.
Claim 14
Dependent Claim
10 words
A process according to claim 2 wherein R is methyl-cyclopropyl.
Claim 15
Dependent Claim
9 words
A process according to claim 2 including compound (b).
Claim 16
Dependent Claim
24 words
A process according to claim 14 wherein R 1 and R 2 are both hydrogen and R 3 and R 4 are both methyl.
Claim 17
Dependent Claim
22 words
A process according to claim 15 wherein there are used 1.5 to 2 moles of compound (IV) per mole of acyl cyanide.
Claim 18
Dependent Claim
21 words
A process according to claim 14 wherein there are used 1 to 10 moles of acid per mole of acyl cyanide.
Claim 19
Dependent Claim
17 words
A process according to claim 17 wherein the acid is sulfuric acid or an organic sulfonic acid.
Claim 20
Dependent Claim
21 words
A process according to claim 18 wherein there are used 1.1 to 1.5 moles of acid per mole of acyl cyanide.
Claim 21
Dependent Claim
22 words
A process according to claim 19 wherein there are employed 1.5 to 2 moles of compound (IV) per mole of acyl cyanide.
Claim 22
Dependent Claim
18 words
A process according to claim 18 wherein the methylating agent is methyl bromide, methyl iodide or dimethyl sulfate.
Claim 23
Dependent Claim
10 words
A process according to claim 1 which includes steps (2).
Claim 24
Dependent Claim
9 words
A process according to claim 22 including compound (a).
Claim 25
Dependent Claim
13 words
A process according to claim 23 wherein R' is t-amyl, t-octyl or t-butyl.
Claim 26
Dependent Claim
22 words
A process according to claim 23 wherein there are employed 1.5 to 2 moles of compound (III) per mole of acyl cyanide.
Claim 27
Dependent Claim
27 words
A process according to claim 23 wherein there are employed 1 to 10 moles of sulfuric acid or an organic sulfonic acid per mole of acyl cyanide.
Claim 28
Dependent Claim
34 words
A process according to claim 26 wherein there are used 1.1 to 1.5 moles of acid per mole of acyl cyanide and 1.5 to 2 moles of compound (III) per mole of acyl cyanide.
Claim 29
Dependent Claim
10 words
A process according to claim 22 wherein R is t-butyl.
Claim 30
Dependent Claim
10 words
A process according to claim 22 wherein R is methyl-cyclopropyl.
Claim 31
Dependent Claim
9 words
A process according to claim 22 including compound (b).
Claim 32
Dependent Claim
24 words
A process according to claim 30 wherein R 1 and R 2 are both hydrogen and R 3 and R 4 are both methyl.
Claim 33
Dependent Claim
27 words
A process according to claim 30 wherein there is used 1 to 10 moles of sulfuric acid or an organic sulfonic acid per mole of acyl cyanide.
Claim 34
Dependent Claim
34 words
A process according to claim 32 wherein there are used 1.1 to 1.5 moles of acid per mole of acyl cyanide and 1.5 to 2 moles of compound (IV) per mole of acyl cyanide.
Claim 35
Dependent Claim
22 words
A process according to claim 30 wherein there are used 1.5 to 2 moles of compound (IV) per mole of acyl cyanide.
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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) | 1982-11-19 | 1983-05-21 | 1983-11-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-11-19 | 1987-05-21 | 1987-11-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-11-19 | 1991-05-21 | 1991-11-20 | $7700.00 | Window Closed / Lapsed |