JP-7855014-B2 - Method for producing 2-alkylthio-1-imidazoylethanone compounds

Inventors

• 安田 幸平
• 白田 浩

Assignees

• 日本曹達株式会社

Dates

Publication Date

20260507

Application Date

20221116

Priority Date

20211119

Claims (5)

1. Compound represented by formula (1): (In formula (1) above, R1 represents a C1-6 alkyl group, R2 represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a 1,3-dioxolan-2-yl group, and Ra represents a C1-6 alkyl group) Compound represented by formula (2): (In formula (2) above, R3 represents a C1-6 alkyl group, and Rb represents a C1-6 alkyl group) The chemical reaction of a Lewis acid and a base in the presence of a Lewis acid and a base. Compounds represented by formula (3), including: A method for manufacturing (in formula (3), R1 , R2 , R3 , and Rb are the same as those in formula (1) and formula (2) above).
2. The Lewis acid is a Ti compound represented by formula (4): The manufacturing method according to claim 1, wherein in formula (4) above, X represents a halogeno group, R c represents a C1-6 alkyl group, m is an integer from 0 to 4, n is an integer from 0 to 4, and m + n = 4.
3. Compound represented by formula (3a): (In formula (3a) above, R 1a represents a C1-6 alkyl group, R 2a represents a C2-6 haloalkenyl group, R 3a represents a C1-6 alkyl group, and R ba represents a C1-6 alkyl group).
4. Compound represented by formula (1a): (In formula (1a) above, R 1a represents a C1-6 alkyl group, R 2a represents a C2-6 haloalkenyl group, and Raaa represents a C1-6 alkyl group).
5. A chloroformate ester represented by the formula: ClCO₂R aa (wherein R aa represents a C1-6 alkyl group) Compound represented by formula (7): (In formula (7) above, R 1a represents a C1-6 alkyl group, and R 2a represents a C2-6 haloalkenyl group.) The addition step involves adding it to a mixture of diisopropylethylamine and chloroform, The compound represented by formula (7) and the chloroformate ester are reacted in the presence of the diisopropylethylamine to obtain the compound represented by formula (1a): (In formula (1a) above, R 1a represents a C1-6 alkyl group, R 2a represents a C2-6 haloalkenyl group, and Raaa represents a C1-6 alkyl group.) A method for producing a compound represented by formula (1a), comprising a reaction step to obtain [the compound].

Description

This invention relates to a method for producing 2-alkylthio-1-imidazoylethanone compounds. This application claims priority based on Japanese Patent Application No. 2021-188983, filed in Japan on November 19, 2021, and the contents of that application are incorporated herein by reference. Nitrogen-containing heterocycles are major substructures (building blocks) that constitute compounds that are the active ingredients of pharmaceuticals and agrochemicals. In recent years, there has been a great deal of activity in developing pest control agents for arthropods that contain imidazole rings, pyridine rings, etc. For example, Patent Document 1 discloses an ethylsulfonyl-substituted imidazoylpyrimidine compound, and shows a compound represented by formula (A) as a manufacturing intermediate thereto. Patent Document 1 discloses that a compound represented by formula (A) was produced by the following process. Furthermore, Patent Document 2 discloses that imidazole compounds were manufactured by the following process. Furthermore, Patent Document 3 discloses that imidazole compounds were manufactured by the following process. WO 2020/071304AWO 2005/090333AJapanese Patent Publication No. 2017-66077 A In this invention, the term "unsubstituted" means that only the core group is present. When the term "substituted" is not used and only the name of the core group is given, it means "unsubstituted" unless otherwise specified. On the other hand, the term "substitution" means that one of the hydrogen atoms of the core group is substituted by a group (substituent) that has the same or different structure as the core group. Therefore, a "substituent" is another group bonded to the core group. There may be one substituent or two or more substituents. The two or more substituents may be the same or different. Terms such as "C1-C6" indicate that the parent group has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms in substituents. For example, a butyl group with an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group. The "substituents" are chemically acceptable and not particularly limited insofar as they have the effects of the present invention. The following are examples of groups that can act as "substituents". C1-6 alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, and n-hexyl group; C2-6 alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, and 2-methyl-2-propenyl group; C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, and 1-methyl-2-propynyl group; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; Phenyl group; 3- to 6-membered heterocyclyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C6-10 aryloxy groups such as phenoxy and naphthoxy groups; Five- to six-membered heteroaryloxy groups such as thiazolyloxy and pyridyloxy groups; C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, and t-butoxycarbonyl group; Halogeno groups such as fluoro groups, chloro groups, bromo groups, and iod groups; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, and perfluoro-n-pentyl group; C1-6 haloalkoxy groups such as trifluoromethoxy, 2-chloro-n-propoxy, and 2,3-dichlorobutoxy; Formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino groups, propanoylamino groups, butyrylamino groups, and i-propylcarbonylamino groups; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino groups, ethoxycarbonylamino groups, n-propoxycarbonylamino groups, and i-propoxycarbonylamino groups; Unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl groups, dimethylaminocarbonyl groups, phenylaminocarbonyl groups, and N-phenyl-N-methylaminocarbonyl groups; C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, and t-butylthio group; C1-6 haloalkylthio groups such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group; C1-6 alkylsulfonyl groups such as methylsulfonyl groups, ethylsulfonyl groups, and t-butylsulfonyl groups; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group; Cyano group; nitro group. Furthermore, in these "substituents," any hydrogen atom in the substituent may be substituted with a group of a different structure. Examples of such substituents include C1-6 alkyl groups, C1-