US4013677A
Expired / Lapsed
US
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Preparation of 1,2,4-triazolyl-(1)-phenoxy-acyl-methanes
Assignee: Bayer AG
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Filing: 1975-02-05
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Granted: 1977-03-22
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Expires: 1995-02-05
Abstract
Abstract A process for the preparation of a 1,2,4-triazolyl-(1)-phenoxy-acyl-methane of the formula ##STR1## in which R is alkyl or aryl, Each X independently is alkyl, halogen, alkoxycarbonyl, nitrile, phenyl or nitro, and n is an integer from 0 to 5, Comprising reacting a dihaloketone of the formula (Hal).sub.2 CH--CO--R in which Hal is halogen, ##STR2## 1,2,4-TRIAZOLE AND WITH A PHENOL OF THE FORMULA T,0011 IN THE PRESENCE OF AN ACID-BINDING AGENT AND DILUENT, AT A TEMPERATURE OF ABOUT 0° TO 150° C. Advantageously the temperature is about 50° to 90° C and about 1 mole of the phenol, about 1 to 1.2 moles of the 1,2,4-triazole and about 2 to 3 moles of the acid-binding agent are used per mole of the dihaloketone.
Inventors
- 👤 Claus Stolzer
- 👤 Wolfgang Kramer
- 👤 Karl Heinz Buchel
- 👤 Werner Meiser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 05:00
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A61; A61P; A61P31/00; A61P31/10; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
125 words
A process for the preparation of a 1,2,4-triazolyl-(1)-phenoxy-acyl-methane of the formula ##STR10## in which R is alkyl with 1 to 4 carbon atoms or phenyl, each X independently is alkyl with 1 to 4 carbon atoms, halogen, alkoxycarbonyl with 1 or 2 carbon atoms in the alkoxy, nitrile, phenyl or nitro, and n is an integer from 0 to 5, comprising reacting a dihaloketone of the formula (Hal).sub.2 CH--CO--R in which Hal is halogen, with 1,2,4-triazole and with a phenol of the formula ##STR11## in the presence of an acid-binding agent selected from the group consisting of alkali metal and alkaline earth metal hydroxides and carbonates and tertiary amines and a polar organic solvent as diluent, at a temperature of about 0° to 150° C.
Claim 2
Dependent Claim
125 words
A process for the preparation of a 1,2,4-triazolyl-(1)-phenoxy-acyl-methane of the formula ##STR10## in which R is alkyl with 1 to 4 carbon atoms or phenyl, each X independently is alkyl with 1 to 4 carbon atoms, halogen, alkoxycarbonyl with 1 or 2 carbon atoms in the alkoxy, nitrile, phenyl or nitro, and n is an integer from 0 to 5, comprising reacting a dihaloketone of the formula (Hal).sub.2 CH--CO--R in which Hal is halogen, with 1,2,4-triazole and with a phenol of the formula ##STR11## in the presence of an acid-binding agent selected from the group consisting of alkali metal and alkaline earth metal hydroxides and carbonates and tertiary amines and a polar organic solvent as diluent, at a temperature of about 0° to 150° C.
Claim 3
Dependent Claim
19 words
A process according to claim 1 in which the reaction is carried out at about 50° to 90° C.
Claim 4
Dependent Claim
39 words
A process according to claim 1 in which about 1 mole of the phenol, about 1 to 1.2 moles of the 1,2,4-triazole and about 2 to 3 moles of the acid-binding agent are used per mole of the dihaloketone.
Claim 5
Dependent Claim
45 words
A process according to claim 1, Hal is chlorine, each X independently is alkyl with 1 to 4 carbon atoms, chlorine, fluorine, bromine, alkoxycarbonyl with 1 or 2 carbon atoms in the alkoxy, phenyl, nitrile or nitro, and n is 0, 1, 2 or 3.
Claim 6
Dependent Claim
51 words
A process according to claim 4 in which the reaction is carried out at about 50° to 90° C, and about 1 mole of the phenol, about 1 to 1.2 moles of the 1,2,4-triazole and about 2 to 3 moles of the acid-binding agent are used per mole of the dihaloketone.
Claim 7
Dependent Claim
16 words
A process according to claim 1 in which R is tert. butyl and X is 4-chloro.
Claim 8
Dependent Claim
16 words
A process according to claim 1 in which R is tert. butyl and X is 4-phenyl.
Claim 9
Dependent Claim
16 words
A process according to claim 1 in which R is tert. butyl and X is 2,4-dichloro.
Claim 10
Dependent Claim
16 words
A process according to claim 1 in which R is tert. butyl and X is 4-bromo.
Claim 11
Dependent Claim
16 words
A process according to claim 1 in which R is tert. butyl and X is 4-fluoro.
References Cited (Backward Citations)
US3912752A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-21 | 1980-09-20 | 1981-03-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-21 | 1984-09-20 | 1985-03-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-21 | 1988-09-20 | 1989-03-22 | $7700.00 | Window Closed / Lapsed |