Method for producing compound

Patent metadata

Field	Value
Publication number	US-12428387-B2
Application number	US-202118040365-A
Country	US
Kind code	B2
Filing date	Aug 6, 2021
Priority date	Aug 6, 2020
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

A method by which an intermediate product of an azole derivative can be produced at a lower cost than known production methods is provided. A method for producing a compound represented by General Formula (IV) includes converting a compound represented by General Formula (II) into the compound represented by General Formula (IV) using (a) dimethyl sulfide and/or dimethyl sulfoxide, and (b) a methyl-LG (an LG is a nucleophilically substitutable leaving group and is selected from the group consisting of a halogen group, an alkoxysulfonyloxy group, an aryloxysulfonyloxy group, an alkylsulfonyloxy group, a haloalkylsulfonyloxy group, and an arylsulfonyloxy group) in the presence of an inorganic base.

First claim

The invention claimed is:

1. A method for producing a compound represented by General Formula (IV):

where in General Formula (IV), R 1 is a C 1 -C 6 -alkyl group;
X 1 is a halogen group, a C 1 -C 4 -haloalkyl group, or a C 1 -C 4 -haloalkoxy group;
X 2 is a halogen group, a C 1 -C 4 -haloalkyl group, or a C 1 -C 4 -haloalkoxy group; and
n is 1, 2, or 3;
the method comprising converting a compound represented by General Formula (III) into a compound represented by General Formula (II):

where in Formula (II), R 1 , X 1 , X 2 , and n are respectively the same as R 1 , X 1 , X 2 and n in Formula (IV),

where in Formula (III), X 1 , X 2 , and n are respectively the same as X 1 , X 2 , and n in Formula (IV),

wherein, in the converting step, in a solvent containing dimethyl sulfoxide, bromine is allowed to react with the compound represented by General Formula (III) while a reaction system is heated, and subsequently R 1 —OH (where R 1 is the same as R 1 in Formula (IV)) is allowed to react, and thus the compound represented by General Formula (II) is formed,
wherein the step of converting into the compound represented by General Formula (II) is performed in the presence of at least one selected from the group consisting of urea, adipic acid dihydrazide, and dibutylhydroxytoluene,
the method further comprising converting thea compound represented by General Formula (II) into the compound represented by General Formula (IV) using:
(a) dimethyl sulfide and/or dimethyl sulfoxide, and
(b) a methyl-LG, where LG is a nucleophilically substitutable leaving group and is selected from the group consisting of a halogen group, an alkoxysulfonyloxy group, an aryloxysulfonyloxy group, an alkylsulfonyloxy group, a haloalkylsulfonyloxy group, and an arylsulfonyloxy group
in the presence of an inorganic base.

2. The method according to claim 1 , wherein, in the step of converting into the compound represented by General Formula (IV), amounts required for a reaction of the (a) and the (b) are divided and added in multiple batches.

3. The method according to claim 1 , wherein the (a) is dimethyl sulfide and dimethyl sulfoxide both.

4. The method according to claim 1 , wherein, in the step of converting into the compound represented by General Formula (II), in the solvent containing dimethyl sulfoxide, after a reaction system to which bromine is added is heated, the bromine is allowed to react with the compound represented by General Formula (III) by adding the compound represented by General Formula (III), and subsequently R 1 —OH (where R 1 is the same as R 1 in Formula (IV)) is allowed to react, and thus the compound represented by General Formula (II) is formed.

5. A method for producing a compound represented by General Formula (I), comprising the method for producing the compound represented by General Formula (IV) according to claim 1 , and
converting the compound represented by General Formula (IV) obtained by the method into the compound represented by General Formula (I) using 1,2,4-triazole in the presence of an inorganic base:

where R 1 , X 1 , X 2 , and n in Formula (I) are respectively the same as R 1 , X 1 , X 2 , and n in Formula (IV).

Assignees

• Kureha Corp

Inventors

• Harigae Ryo
• Kojima Chiemi
• Konno Shingo
• Yamazaki Toru

Classifications

• C07D303/48 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals · CPC title

• C07D249/08

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

• C07C67/42

  by oxidation of secondary alcohols or ketones · CPC title

• C07C45/63

  by introduction of halogen; by substitution of halogen atoms by other halogen atoms · CPC title

• C07C67/27

  from ortho-esters · CPC title