Process for the preparation of substituted oxiranes and triazoles

Patent metadata

Field	Value
Publication number	US-10981883-B2
Application number	US-201916694296-A
Country	US
Kind code	B2
Filing date	Nov 25, 2019
Priority date	Jan 9, 2013
Publication date	Apr 20, 2021
Grant date	Apr 20, 2021

Abstract

The present invention relates to a process for the preparation of the compounds II

from the respective oxo compounds. Furthermore, the invention relates to a process for the preparation of triazole compounds from oxiranes II.

First claim

The invention claimed is:

1. A process for the preparation of a triazole compound of formula I

comprising
(iia) reacting a compound of formula II

with 1H-1,2,4-triazole and an inorganic base, wherein the amount of the inorganic base is less than 1 equivalent of said base per 1 equivalent of compound II, resulting in the compound of formula I,
wherein
R 1 is selected from C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, phenyl, phenyl-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl or phenyl-C 1 -C 4 -alkynyl;
wherein the aliphatic moieties of R 1 are not further substituted or do carry one, two, three or up to the maximum possible number of identical or different groups R 12a which independently are selected from:
R 12a halogen, OH, CN, nitro, C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and C 1 -C 4 -halogenalkoxy;
wherein the cycloalkyl and/or phenyl moieties of R 1 are not further substituted or do carry one, two, three, four, five or up to the maximum number of identical or different groups R 12b which independently are selected from:
R 12b halogen, OH, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and C 1 -C 4 -halogenalkoxy
R 3 is independently selected from halogen, CN, NO 2 , OH, SH, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , S(O) p (C 1 -C 4 -alkyl), C(═O)(C 1 -C 4 -alkyl), C(═O)(OH), C(═O)(O—C 1 -C 4 -alkyl), C(═O)(NH(C 1 -C 4 -alkyl)), C(═O)(N(C 1 -C 4 -alkyl) 2 ), C(═O)(NH(C 3 -C 6 -cycloalkyl)) and C(═O)—(N(C 3 -C 6 -cycloalkyl) 2 ); wherein p is 0, 1 or 2; and wherein each of R 3 is unsubstituted or further substituted by one, two, three or four R 3 ; wherein
R 3a is independently selected from halogen, CN, NO 2 , OH, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy;
R 4 is independently selected from the substituents as defined for R 3 , wherein said R 4 are unsubstituted or further substituted by one, two, three or four R 4a , wherein each R 4a is independently selected from the substituents as defined for R 3a ;
n is 0, 1, 2, 3 or 4; and
m is 0, 1, 2, 3, 4 or 5, wherein the product resulting from step (iia) is crystallized from toluene and/or an aliphatic alcohol.

2. The process of claim 1 , wherein the aliphatic alcohol is selected from methanol, ethanol, n-propanol, iso-propanol, n-butanol, isobutanol or any mixture thereof.

3. The process of claim 1 , wherein the base used in step (iia) is selected from NaOH, KOH, Na 2 CO 3 and K 2 CO 3 .

4. The process of claim 1 , wherein the base used in step (iia) is selected from NaOH and KOH.

5. The process of claim 1 , wherein the amount of base used in step (iia) is equal to or less than 0.6 equivalents per 1 equivalent of compound II.

Assignees

• Basf Agro Bv

Inventors

• Zierke Thomas
• Gebhardt Joachim
• Schaefer Peter
• Vogelbacher Uwe Josef
• Rack Michael
• Lohmann Jan Klaas

Classifications

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07D249/08 Primary

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• A01N43/653 Primary

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• C07D249/04

  1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles · CPC title

• C07D303/23

  Oxiranylmethyl ethers of compounds having one hydroxy group bound to a six-membered aromatic ring, the oxiranylmethyl radical not being further substituted, i.e. [IMAGE cpc-sch-C07D-1030.gif] · CPC title