Method for producing sulfoxide derivative

Patent metadata

Field	Value
Publication number	US-10577313-B2
Application number	US-201716080923-A
Country	US
Kind code	B2
Filing date	Feb 28, 2017
Priority date	Mar 3, 2016
Publication date	Mar 3, 2020
Grant date	Mar 3, 2020

Abstract

A method for producing a sulfoxide derivative represented by general formula (1),

the method being characterized in that a sulfide derivative represented by general formula (2)

is reacted with an oxidizing agent in the presence of a catalyst that is a metal-ligand complex containing a metal compound and, as a ligand, a compound represented by general formula (3),

and in the presence of a benzoic acid compound represented by general formula (4)

First claim

The invention claimed is:

1. A method for producing a sulfoxide derivative represented by general formula (1):

(wherein,
R 1 is a C1 to C10 alkyl group,
a C3 to C6 cycloalkyl C1 to C6 alkyl group, wherein the said C3 to C6 cycloalkyl group moiety may be monosubstituted or polysubstituted by a halogen atom, a C1 to C4 alkyl group, a C1 to C4 alkoxy group or C1 to C4 haloalkyl group,
a phenyl C1 to C6 alkyl group, wherein the said phenyl group moiety may be monosubstituted or polysubstituted by a halogen atom, a C1 to C4 alkyl group, a C1 to C4 alkoxy group, a C1 to C6 haloalkyl group, a cyano group or a nitro group,
a C1 to C4 alkoxy C2 to C10 alkyl group,
a C1 to C4 haloalkoxy C2 to C10 alkyl group,
a C1 to C4 alkylthio C2 to C10 alkyl group,
a C1 to C4 alkylsulfinyl C2 to C10 alkyl group,
a C1 to C4 alkyl sulfonyl C2 to C10 alkyl group,
a C1 to C4 haloalkylthio C2 to C10 alkyl group,
a C1 to C4 haloalkylsulfinyl C2 to C10 alkyl group,
a C1 to C4 haloalkylsulfonyl C2 to C10 alkyl group,
a C1 to C6 haloalkyl group,
a C3 to C6 cycloalkyl C1 to C6 haloalkyl group wherein the said C3 to C6 cycloalkyl group moiety may be monosubstituted or polysubstituted by a halogen atom, a C1 to C4 alkyl group, a C1 to C4 alkoxy group or a C1 to C6 haloalkyl group,
a phenyl C1 to C6 haloalkyl group, wherein the said phenyl moiety may be monosubstituted or polysubstituted by a halogen atom, a C1 to C4 alkyl group, a C1 to C4 alkoxy group, a C1 to C4 haloalkyl group, a cyano group or a nitro group, or
a C1 to C4 haloalkylthio C1 to C6 haloalkyl group;
R 2 and R 3 are each independently a hydrogen atom, a halogen atom or a C1 to C4 alkyl group), which comprises reacting a sulfide derivative represented by general formula (2):

(wherein, R 1 , R 2 and R 3 are as defined above) with an oxidizing agent in the presence of both a catalyst which is a metal-ligand complex containing a metal compound and
a ligand compound represented by general formula (3):

which is selected from the group consisting of

 and
a benzoic acid compound represented by general formula (4):

(wherein,
A 1 is a C1 to C2 alkoxy group;
A 2 is a hydrogen atom;
A 3 is a hydrogen atom or a C1 to C2 alkoxy group;
A 4 is a hydrogen atom;
A 5 is a C1 to C2 alkoxy group;
M is a hydrogen atom, an alkali metal atom or an alkaline earth metal atom; and
n is 1 or 2).

2. The method according to claim 1 , wherein
R 1 is a C1 to C10 alkyl group,
a C3 to C6 cycloalkyl C1 to C6 alkyl group, wherein the said C3 to C6 cycloalkyl group moiety may be monosubstituted or polysubstituted by a halogen atom or a C1 to C4 alkyl group,
a phenyl C1 to C6 alkyl group, wherein the said phenyl group moiety may be monosubstituted or polysubstituted by a halogen atom or a C1 to C4 alkyl group,
a C1 to C4 alkoxy C2 to C10 alkyl group,
a C1 to C4 haloalkoxy C2 to C10 alkyl group,
a C1 to C4 alkylthio C2 to C10 alkyl group,
a C1 to C4 alkylsulfinyl C2 to C10 alkyl group,
a C1 to C4 alkylsulfonyl C2 to C10 alkyl group,
a C1 to C4 haloalkylthio C2 to C10 alkyl group,
a C1 to C4 haloalkylsulfinyl C2 to C10 alkyl group,
a C1 to C4 haloalkylsulfonyl C2 to C10 alkyl group,
a C1 to C6 haloalkyl group,
a C3 to C6 cycloalkyl C1 to C6 haloalkyl group, wherein the said C3 to C6 cycloalkyl group moiety may be monosubstituted or polysubstituted by a halogen atom or a C1 to C4 alkyl group, or a phenyl C1 to C6 haloalkyl group, wherein the said phenyl group moiety may be monosubstituted or polysubstituted by a halogen atom or a C1 to C4 alkyl group.

3. The method according to claim 1 , wherein
R 1 is a C1 to C10 alkyl group,
a C1 to C4 alkoxy C2 to C10 alkyl group,
a C1 to C4 haloalkoxy C2 to C10 alkyl group,
a C1 to C4 alkylthio C2 to C10 alkyl group,
a C1 to C4 alkylsulfinyl C2 to C10 alkyl group,
a C1 to C4 alkylsulfonyl C2 to C10 alkyl group,
a C1 to C4 haloalkylthio C2 to C10 alkyl group,
a C1 to C4 haloalkylsulfinyl C2 to C10 alkyl group,
a C1 to C4 haloalkylsulfonyl C2 to C10 alkyl group, or
a C1-C6 haloalkyl group.

4. The method according to claim 1 , wherein R 1 is a C1 to C4 haloalkylthio C2 to C10 alkyl group; and R 2 and R 3 are each independently a halogen atom or a C1 to C4 alkyl group.

5. The method according to claim 1 , wherein R 1 is a 5-trifluoromethylthiopentyl group or a 6-trifluoromethylthiohexyl group; and either R 2 is a fluorine atom and R 3 is a chlorine atom, or R 2 and R 3 are methyl groups.

6. The method according to claim 1 , wherein R 1 is a 5-trifluoromethylthiopentyl group; R 2 is a fluorine atom; and R 3 is a chlorine atom.

7. The method according to claim 1 , wherein R 1 is a 6-trifluoromethylthiohexyl group; and R 2 and R 3 are methyl groups.

8. The method according to claim 1 , wherein the metal compound is an iron compound.

9. The method according to claim 1 , wherein
a ligand compound represented by general formula (3):

10. The method according to claim 1 , wherein M is an alkali metal atom; and n is 1.

11. The method according to claim 1 , wherein M is a sodium atom; and n is 1.

12. The method according to claim 1 , wherein
A 1 is a methoxy group;
A 2 is a hydrogen atom;
A 3 is a hydrogen atom or a methoxy group;
A 4 is a hydrogen atom;
A 5 is a methoxy group;
M is a sodium atom; and n is 1.

13. The method according to claim 1 , wherein
A 1 is a methoxy group;
A 2 is a hydrogen atom;
A 3 is a hydrogen atom;
A 4 is a hydrogen atom;
A 5 is a methoxy group;
M is a sodium atom; and n is 1.

14. The method according to claim 1 , wherein
A 1 is a methoxy group;
A 2 is a hydrogen atom;
A 3 is a methoxy group;
A 4 is a hydrogen atom;
A 5 is a methoxy group;
M is a sodium atom; and n is 1.

Assignees

• Kumiai Chemical Industry Co

Inventors

• YASUMURA Shingo

Classifications

• C07C317/22

  with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

• C07B61/00

  Other general methods · CPC title

• C07C319/20

  by reactions not involving the formation of sulfide groups · CPC title

• B01J31/2282

  Unsaturated compounds used as ligands · CPC title

• B01J31/2226

  Anionic ligands, i.e. the overall ligand carries at least one formal negative charge · CPC title