JP-7855012-B2 - Method for producing halovinylimidazole compounds

Inventors

• 江住 直人
• 多田隈 太輝

Assignees

• 日本曹達株式会社

Dates

Publication Date

20260507

Application Date

20221116

Priority Date

20211119

Claims (3)

1. Compound represented by formula (1): (In formula (1), R1 represents a C1-6 alkyl group, Q represents a hydrogen atom or a substituted or unsubstituted pyridyl group, X represents a halogeno group, and Ra represents a C1-6 alkyl group.) Sodium hypochlorite and This includes carrying out chemical reactions in the presence of a base. Compound represented by formula (2): (In equation (2), R1 and Q represent the same values as those in equation (1).) A method for manufacturing this product.
2. Compound represented by formula (3): (In formula (3), R1 represents a C1-6 alkyl group, and Q represents a hydrogen atom or a substituted or unsubstituted pyridyl group.) Compound represented by formula (4): (In formula (4), X represents a halogeno group) and To carry out a chemical reaction in the presence of a base or a metal alkoxide, and the product of the above chemical reaction, Compound represented by formula (5): (In formula (5), Ra represents a C1-6 alkyl group) and The manufacturing method according to claim 1, further comprising obtaining a compound represented by formula (1) by a method including a chemical reaction.
3. Compounds represented by formula (2a1), formula (2a2), or formula (2a3): (In formulas (2a1), (2a2), or (2a3), R1 represents a C1-6 alkyl group).

Description

This invention relates to a method for producing halovinylimidazole compounds. This application claims priority based on Japanese Patent Application No. 2021-188984, 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 active development of pest control agents for harmful arthropods that contain imidazole rings, pyridine rings, etc. For example, Patent Document 1 shows a compound represented by formula (A). Vinylimidazole compounds are also useful as monomers used in polymer production. For example, Patent Document 2 discloses a method characterized by dehydrogenating a compound selected from the group consisting of 2-alkylimidazoles and 2-alkylimidazolines in the presence of a dehydrogenation catalyst to produce 2-alkenylimidazoles. Patent Document 3 discloses a method for producing a 1-vinylimidazole derivative, characterized by dehydrating a 2-hydroxyethylimidazole derivative in the liquid phase in the presence of an alkali metal hydroxide or alkoxide. Patent Document 4 discloses a method for producing a vinylimidazole compound by subjecting a hydroxyethyl group-containing imidazole compound to a dehydration reaction in a solvent whose boiling point at atmospheric pressure is 30°C or more higher than the boiling point at atmospheric pressure of the vinylimidazole compound, in the presence of a dehydrating agent. WO 2020/090585AJapanese Unexamined Patent Publication No. 58-210067Japanese Patent Application Publication No. 4-21672Japanese Patent Publication No. 2011-121913 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; A heterocyclyl group with 3 to 6 members; 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, a