US3965094A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the manufacture of 2-aryl-v-triazole
Assignee: Bayer AG
•
Filing: 1973-03-02
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Granted: 1976-06-22
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Expires: 1993-03-02
Abstract
Abstract 2-Aryl-v-triazoles are obtained by reacting α-oximinoaryl-hydrazones of the formula ##EQU1## IN WHICH Ar represents an aromatic-carbocyclic or aromatic-heterocyclic radical, R 1 denotes alkyl, aryl or nitro, R 2 denotes hydrogen, alkyl or aryl and n denotes the numbers 1 or 2 with at least 2 equivalents of an isocyanate or carbamic acid halide or with at least 1 equivalent of a pyrocarbonic acid ester.
Inventors
- 👤 Uwe Claussen
- 👤 Heinrich Gold
- 👤 Josef Schroeder
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:20
CPC Classifications
C; C07; C07D; C07D249/00; C07D249/02; C07D249/04; C07D249/06
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
176 words
In the process of preparing a 2-aryl-1,2,3-triazole of the formula ##EQU4## by heating an α-oximino hydrazone of the formula ##EQU5## in which Ar is an aromatic-carbocyclic or aromatic-heterocyclic radical; R 1 is C 1 -C 4 -alkyl; C 1 -C 4 -alkyl substituted by halogen, OH, COOH or C 1 -C 4 -alkoxy; phenyl; or phenyl substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; and R 2 is hydrogen or R 1 ; and n is the number 1 or 2; the improvement comprising carrying out the reaction in the presence of at least 2 equivalents of Q -- NCO or Z -- NH -- COCl in which Q is hydrogen; C 1 -C 6 -alkyl; C 5 -C 7 -cycloalkyl; phenyl; phenyl substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or nitro; phenylcarbonyl or phenylsulphonyl; and Z is C 1 14 C 6 -alkyl, phenyl, tolyl, or chlorophenyl; or in the presence of at least 1 equivalent of pyrocarbonic acid methyl or ethyl ester.
Claim 2
Dependent Claim
176 words
In the process of preparing a 2-aryl-1,2,3-triazole of the formula ##EQU4## by heating an α-oximino hydrazone of the formula ##EQU5## in which Ar is an aromatic-carbocyclic or aromatic-heterocyclic radical; R 1 is C 1 -C 4 -alkyl; C 1 -C 4 -alkyl substituted by halogen, OH, COOH or C 1 -C 4 -alkoxy; phenyl; or phenyl substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; and R 2 is hydrogen or R 1 ; and n is the number 1 or 2; the improvement comprising carrying out the reaction in the presence of at least 2 equivalents of Q -- NCO or Z -- NH -- COCl in which Q is hydrogen; C 1 -C 6 -alkyl; C 5 -C 7 -cycloalkyl; phenyl; phenyl substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or nitro; phenylcarbonyl or phenylsulphonyl; and Z is C 1 14 C 6 -alkyl, phenyl, tolyl, or chlorophenyl; or in the presence of at least 1 equivalent of pyrocarbonic acid methyl or ethyl ester.
Claim 3
Dependent Claim
29 words
The process of claim 1 conducted in the presence of a basic catalyst selected from the group consisting of alkali metal hydroxides, alkali metal carbonates, pyridine, quinoline and dimethylaniline.
Claim 4
Dependent Claim
22 words
The process of claim 1 in which the reaction is carried out in the presence of at least 2 equivalents of Q-NCO.
Claim 5
Dependent Claim
22 words
The process of claim 1 in which the reaction is carried out in the presence of a solvent as an additional ingredient.
Claim 6
Dependent Claim
15 words
The process of claim 4 in which the solvent is water or a water/alcohol mixture.
Claim 7
Dependent Claim
11 words
The process of claim 4 in which the solvent is dimethylformamide.
Claim 8
Dependent Claim
15 words
The process of claim 1 in which the reaction is conducted between 20°C and 100°C.
References Cited (Backward Citations)
US3666758A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-22 | 1979-12-22 | 1980-06-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-22 | 1983-12-22 | 1984-06-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-22 | 1987-12-22 | 1988-06-22 | $7700.00 | Window Closed / Lapsed |