WO2019193846A1 - 化合物の製造方法及び化合物 - Google Patents

化合物の製造方法及び化合物 Download PDF

Info

Publication number
WO2019193846A1
WO2019193846A1 PCT/JP2019/005765 JP2019005765W WO2019193846A1 WO 2019193846 A1 WO2019193846 A1 WO 2019193846A1 JP 2019005765 W JP2019005765 W JP 2019005765W WO 2019193846 A1 WO2019193846 A1 WO 2019193846A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbon
compound
atom
general formula
Prior art date
Application number
PCT/JP2019/005765
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
航太郎 林
昭佳 山内
悠希 鈴木
洋介 岸川
Original Assignee
ダイキン工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ダイキン工業株式会社 filed Critical ダイキン工業株式会社
Publication of WO2019193846A1 publication Critical patent/WO2019193846A1/ja

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage

Definitions

  • the present disclosure relates to methods for producing compounds and compounds.
  • Patent Document 1 describes a reaction represented by the following formula.
  • An object of the present disclosure is to provide a method for producing a novel compound and a novel compound.
  • the present disclosure provides the following general formula (1): (Wherein R 1 and R 2 are each independently a fluorine atom or an organic group having 6 or less carbon atoms, and may be bonded to each other to form a cyclic structure. R 3 is carbon-carbon unsaturated. Which is an organic group having 7 or less carbon atoms having a bond).
  • step (1) is preferably carried out in the presence of a base (excluding amine (B)).
  • R 3 preferably contains one carbon-carbon double bond or one carbon-carbon triple bond.
  • R 3 is preferably a 2-propenyl group or a 2-propynyl group.
  • R 1 and R 2 are each independently a fluorine atom or an organic group having 6 or less carbon atoms, and may be bonded to each other to form a cyclic structure.
  • R 3 is carbon-carbon unsaturated. And an organic group having 7 or less carbon atoms having a bond).
  • a method for producing a novel compound and a novel compound can be provided.
  • R 1 and R 2 are each independently a fluorine atom or an organic group having 6 or less carbon atoms, and may be bonded to each other to form a cyclic structure.
  • R 3 is carbon-carbon unsaturated.
  • a compound (1) represented by the formula (1) is an organic group having 7 or less carbon atoms having a bond.
  • Compound (1) is a novel compound and the present disclosure also relates to compound (1).
  • R 1 and R 2 are each independently a fluorine atom or an organic group having 6 or less carbon atoms.
  • the organic group as R 1 and R 2 is a group containing at least one carbon atom, and is an atom other than a carbon atom, for example, a hydrogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a halogen atom ( A fluorine atom, a chlorine atom, etc.).
  • the organic group preferably has 1 to 6 carbon atoms, more preferably 1 to 5 carbon atoms, and still more preferably 1 to 3 carbon atoms.
  • Examples of the organic group as R 1 and R 2 include an alkyl group, an alkenyl group, an alkynyl group, and an aryl group, and these groups may have one or more substituents.
  • substituents include a halogen atom, an alkyl group, a fluorinated alkyl group, a group containing a hetero atom, a halogen atom is preferable, and a fluorine atom is more preferable.
  • the alkyl group as R 1 and R 2 preferably has 1 to 6 carbon atoms, more preferably 1 to 5 carbon atoms, and still more preferably 1 to 3 carbon atoms.
  • the alkyl group may have a fluorine atom or a group containing a hetero atom such as a cyano group.
  • the alkyl group may be a cycloalkyl group. Examples of the alkyl group having no fluorine atom include a methyl group (—CH 3 ), an ethyl group (—CH 2 CH 3 ), a propyl group (—CH 2 CH 2 CH 3 ), and an isopropyl group (—CH (CH 3 ) 2.
  • Butyl group (—CH 2 CH 2 CH 2 CH 3 ), sec-butyl group (—CH (CH 3 ) CH 2 CH 3 ), tert-butyl group (—C (CH 3 ) 3 ), cyclopropyl group (—CHCH 2 CH 2 ), a cyanomethyl group (—CH 2 CN) and the like can be mentioned.
  • a methyl group (—CH 3 ), an ethyl group (—CH 2 CH 3 ), a propyl group (—CH 2 CH 2 CH 3 ), and a cyanomethyl group (—CH 2 CN) are preferable.
  • alkyl group having a fluorine atom examples include —CF 3 , —CF 2 H, —CFH 2 , —CF 2 CF 3 , —CH 2 CF 3 , —CH 2 CF 2 H, —CH 2 CFH 2 , —CF 2 CF 2 H, —CF 2 CFH 2 , —CF 2 CH 3 , —CH 2 CF 2 CF 3 , —CH 2 CF 2 CF 2 H, —CH 2 CF 2 CFH 2 , —CH 2 CFHCF 3 , —CH 2 CFHCF 2 H, —CH 2 CFHCFH 2 , —CF 2 CFHCF 3 , —CH (CF 3 ) 2 , —CF (CF 3 ) 2 , —C (CF 3 ) 3 , —CH 2 CF 2 CF 2 CF 3 , —CH 2 CH 2 CF 2 CF 3 and the like.
  • —CH 2 CF 3 , —CH 2 CF 2 H, —CH 2 CFH 2 , —CH 2 CF 2 CF 3 , —CH 2 CF 2 CF 2 H are preferable.
  • the alkyl group a methyl group (—CH 3 ), an ethyl group (—CH 2 CH 3 ), a cyanomethyl group (—CH 2 CN), and —CH 2 CF 3 are particularly preferable.
  • the alkenyl group as R 1 and R 2 is preferably an alkenyl group having 2 to 5 carbon atoms which may have one or more substituents.
  • the alkenyl group preferably has 2 to 4 carbon atoms.
  • Examples of the alkenyl group include an ethenyl group (—CH ⁇ CH 2 ), a 1-propenyl group (—CH ⁇ CH—CH 3 ), a 1-methylethenyl group (—C (CH 3 ) ⁇ CH 2 ), and a 2-propenyl group.
  • alkenyl group may have include a halogen atom, an alkyl group, a fluorinated alkyl group, a group containing a hetero atom, a halogen atom is preferable, and a fluorine atom is more preferable.
  • alkenyl group examples include a 2-propenyl group (—CH 2 —CH ⁇ CH 2 ) and a 2-propenyl group (—CH 2 —CH ⁇ CH 2 ) wherein at least one hydrogen atom is a fluorine atom.
  • a substituted group is preferred, and a 2-propenyl group (—CH 2 —CH ⁇ CH 2 ) is more preferred.
  • the alkynyl group as R 1 and R 2 is preferably a C 2-6 alkynyl group optionally having one or more substituents.
  • the alkynyl group preferably has 2 to 5 carbon atoms, more preferably 2 to 4 carbon atoms.
  • alkynyl group examples include ethynyl group (—C ⁇ CH), 1-propynyl group (—C ⁇ C—CH 3 ), 2-propynyl group (—CH 2 —C ⁇ CH), 1-butynyl group (—C ⁇ C—CH 2 CH 3 ), 2-butynyl group (—CH 2 —C ⁇ C—CH 3 ), 3-butynyl group (—CH 2 CH 2 —C ⁇ CH), 1-pentynyl group (—C ⁇ C—CH 2 CH 2 CH 3 ), 2-pentynyl group (—CH 2 —C ⁇ C—CH 2 CH 3 ), 3-pentynyl group (—CH 2 CH 2 —C ⁇ C—CH 3 ), 4- Examples thereof include a pentynyl group (—CH 2 CH 2 CH 2 —C ⁇ CH) and a group in which at least one hydrogen atom of these groups is substituted with a substituent.
  • alkynyl group may have examples include a halogen atom, an alkyl group, a fluorinated alkyl group, a group containing a hetero atom, a halogen atom and a silyl group are preferable, and a fluorine atom is more preferable.
  • alkynyl group examples include a 2-propynyl group (—CH 2 —C ⁇ CH) and a 2-propynyl group (—CH 2 —C ⁇ CH) in which at least one hydrogen atom is a fluorine atom or a silyl group. And a 2-propynyl group (—CH 2 —C ⁇ CH) is more preferable.
  • the aryl group as R 1 and R 2 is preferably an aryl group having 5 to 7 carbon atoms.
  • the aryl group preferably has 5 to 6 carbon atoms.
  • the aryl group preferably contains a 6-membered aromatic hydrocarbon ring or aromatic heterocycle.
  • Examples of the aryl group include a phenyl group, a benzyl group, a tolyl group, and a pyridyl group, and these groups may have one or more substituents.
  • substituents include a halogen atom, an alkyl group, a fluorinated alkyl group, a group containing a hetero atom, a halogen atom is preferable, and a fluorine atom is more preferable.
  • a phenyl group, a benzyl group, and a pyridyl group are preferable, and a phenyl group and a pyridyl group are more preferable.
  • R 1 and R 2 may be bonded to each other to form a cyclic structure.
  • R 1 and R 2 are bonded to each other to form a 5-membered or 6-membered heterocyclic ring together with the nitrogen atom in the general formula (1) (the nitrogen atom in the amide bond in the general formula (1)).
  • a hydrogen group is preferred.
  • the heterocycle is preferably a non-aromatic heterocycle.
  • the heterocyclic ring preferably has 3 to 5 carbon atoms, and more preferably 4 to 5 carbon atoms.
  • the hydrocarbon group may contain at least one selected from the group consisting of O, S and N in the structure.
  • hydrocarbon group examples include the pyrrolidine ring, piperidine ring, oxazolidine ring, morpholine ring, thiazolidine ring, 2,5-dihydro-1H-pyrrole ring, pyrrole-2,5-dione together with the nitrogen atom in the general formula (1).
  • groups that form a ring, 4,5-dihydro-1H-imidazole ring, and the like are preferable.
  • a group which forms a pyrrolidine ring, piperidine ring or morpholine ring with the nitrogen atom in (1) is more preferred.
  • R 1 and R 2 are, among others, an alkyl group which may have a fluorine atom, a hydrocarbon which is bonded to each other to form a 5-membered or 6-membered heterocyclic ring together with the nitrogen atom in the general formula (1) Groups are preferred.
  • R 3 is an organic group having 7 or less carbon atoms having a carbon-carbon unsaturated bond.
  • the organic group as R 3 is a group containing at least one carbon-carbon unsaturated bond, and is an atom other than a carbon atom, for example, a hydrogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a halogen atom ( A fluorine atom, a chlorine atom, etc.).
  • the carbon-carbon unsaturated bond is preferably a carbon-carbon double bond (—C ⁇ C—) or a carbon-carbon triple bond (—C ⁇ C—).
  • the organic group preferably has 2 to 6 carbon atoms, more preferably 2 to 5 carbon atoms, and still more preferably 2 to 4 carbon atoms.
  • Examples of the organic group as R 3 include an alkenyl group, an alkynyl group, and an aryl group, and these groups optionally have one or more substituents.
  • substituents include a halogen atom, an alkyl group, a fluorinated alkyl group, a group containing a hetero atom, a halogen atom is preferable, and a fluorine atom is more preferable.
  • the alkenyl group as R 3 is preferably an alkenyl group having 2 to 5 carbon atoms which may have one or more substituents.
  • Examples of the alkenyl group include an ethenyl group (—CH ⁇ CH 2 ), a 1-propenyl group (—CH ⁇ CH—CH 3 ), a 1-methylethenyl group (—C (CH 3 ) ⁇ CH 2 ), and a 2-propenyl group.
  • alkenyl group may have include a halogen atom, an alkyl group, a fluorinated alkyl group, a group containing a hetero atom, a halogen atom is preferable, and a fluorine atom is more preferable.
  • the alkenyl group is also preferably an alkenyl group having a fluorine atom.
  • the alkenyl group having a fluorine atom include an ethenyl group (—CH ⁇ CH 2 ), a 1-propenyl group (—CH ⁇ CH—CH 3 ), a 1-methylethenyl group (—C (CH 3 ) ⁇ CH 2 ), 2-propenyl group (allyl group, —CH 2 —CH ⁇ CH 2 ), 1-butenyl group (—CH ⁇ CH—CH 2 CH 3 ), 2-methyl-1-propenyl group (—CH ⁇ C (CH 3 ) —CH 3 ), 1-methyl-1-propenyl group (—C (CH 3 ) ⁇ CH—CH 3 ), 1-ethylethenyl group (—C (CH 2 CH 3 ) ⁇ CH 2 ), 2-butenyl group (—CH 2 —CH ⁇ CH—CH 3 ), 2-methyl-2-propenyl group (—CH 2 —C (CH
  • alkenyl groups those containing one carbon-carbon double bond are preferable.
  • the alkynyl group as R 3 is preferably a C 2-6 alkynyl group which may have one or more substituents.
  • Examples of the alkynyl group include an ethynyl group (—C ⁇ CH), a 1-propynyl group (—C ⁇ C—CH 3 ), a 2-propynyl group (propargyl group, —CH 2 —C ⁇ CH), and a 1-butynyl group.
  • alkynyl group may have examples include a halogen atom, an alkyl group, a fluorinated alkyl group, a group containing a hetero atom, a halogen atom and a silyl group are preferable, and a fluorine atom is more preferable.
  • the alkynyl group is also preferably an alkynyl group having a fluorine atom.
  • alkynyl group having a fluorine atom examples include ethynyl group (—C ⁇ CH), 1-propynyl group (—C ⁇ C—CH 3 ), 2-propynyl group (—CH 2 —C ⁇ CH), 1-butynyl.
  • alkynyl groups those containing one carbon-carbon triple bond are preferable, Ethynyl group (—C ⁇ CH), 1-propynyl group (—C ⁇ C—CH 3 ), 2-propynyl group (—CH 2 —C ⁇ CH), 1-butynyl group (—C ⁇ C—CH 2 CH 3 ), 2-butynyl group (—CH 2 —C ⁇ C—CH 3 ), 2-pentynyl group (—CH 2 —C ⁇ C—CH 2 CH 3 ), and at least one hydrogen atom in these groups Is more preferably a group substituted by a fluorine atom or a silyl group, -C ⁇ C-TMS, -C ⁇ C-F, 1-propynyl group (-C ⁇ C-CH 3 ), -C ⁇ C-CF 3 , 2-propynyl group (-CH 2 -C ⁇ CH), A group in which at least one hydrogen atom is substituted with a fluorine atom or
  • the aryl group as R 3 is preferably an aryl group having 6 to 7 carbon atoms.
  • the aryl group preferably contains a 6-membered aromatic hydrocarbon ring.
  • aryl group examples include a phenyl group, a benzyl group, and a tolyl group, and these groups optionally have one or more substituents.
  • substituents include a halogen atom, an alkyl group, a fluorinated alkyl group, a group containing a hetero atom, a halogen atom is preferable, and a fluorine atom is more preferable.
  • aryl groups a phenyl group and a benzyl group are preferable.
  • R 3 preferably contains one carbon-carbon double bond or one carbon-carbon triple bond, or an alkenyl group having 2 to 6 carbon atoms containing one carbon-carbon double bond, or a carbon-carbon triple bond. It is more preferably an alkynyl group having 2 to 6 carbon atoms containing one of them, more preferably a 2-propenyl group or a 2-propynyl group.
  • the compound represented by a following formula can be illustrated, for example.
  • the illustration of the compound in this specification shall also include the geometric isomer (when it exists) of the said compound, and is not limited to the specific example described.
  • a compound represented by the following formula is particularly preferable.
  • the production method of the present disclosure includes the following general formula (A): (Wherein R 3 is the same as described above. X is a halogen atom) and the following general formula (B): (In the formula, R 1 and R 2 are the same as above.)
  • a step (1) of obtaining compound (1) by reacting with amine (B) represented by the formula (1) is included.
  • amine (B) represented by the formula (1) may polymerize during the reaction.
  • a transesterification method is also conceivable as another method for synthesizing the compound (1).
  • a diamine compound may be formed (for example, the mechanism is described by Testa, Maria Luisa; Zaballos,von; Zaragoza).
  • the production method of the present disclosure includes the step (1), and surprisingly, there are few by-products such as a diamine body, the polymerization reaction due to the unsaturated bond hardly occurs, and high purity (for example, GC purity 95). 0.0% or more) of compound (1) can be produced.
  • X is a halogen atom.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among them, a fluorine atom and a chlorine atom are preferable.
  • R 3 in the general formula (A) and R 1 and R 2 in the general formula (B) are as described for the general formula (1).
  • step (1) 1.0 to 1.5 mol of amine (B) is preferably used relative to 1 mol of compound (A), more preferably 1.0 to 1.2 mol. preferable.
  • the reaction in step (1) is preferably carried out in the presence of a base (excluding amine (B)).
  • a base excluding amine (B)
  • An amine however, except amine (B)), an inorganic base, etc. are mentioned.
  • the amine include tertiary amines and pyridines (pyridine and derivatives thereof).
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • DBU 5-diazabicyclo [4.3.0] -5-nonene
  • Examples of the inorganic base include lithium hydroxide, potassium hydroxide, sodium hydroxide, calcium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, cesium carbonate, cesium bicarbonate, and hydrogen carbonate.
  • Examples thereof include lithium, cesium fluoride, potassium fluoride, sodium fluoride, lithium chloride, and lithium bromide.
  • the above amine is preferable, at least one selected from the group consisting of tertiary amines and pyridines is more preferable, and at least one selected from the group consisting of triethylamine and pyridine is more preferable. .
  • the base is preferably used in an amount of 1.0 to 1.5 mol, more preferably 1.0 to 1.2 mol, per 1 mol of compound (A).
  • the reaction of step (1) can be carried out in a solvent.
  • the solvent is preferably an organic solvent, and examples thereof include non-aromatic hydrocarbon solvents, aromatic hydrocarbon solvents, ketone solvents, halogenated hydrocarbon solvents, ether solvents, ester solvents, nitrile solvents, sulfoxide solvents, and amide solvents. It is done.
  • non-aromatic hydrocarbon solvents such as pentane, hexane, heptane, octane, cyclohexane, decahydronaphthalene, n-decane, isododecane and tridecane; benzene, toluene, xylene, tetralin, veratrol, diethylbenzene, methylnaphthalene, Aromatic hydrocarbon solvents such as nitrobenzene, o-nitrotoluene, mesitylene, indene, diphenyl sulfide; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, propiophenone, diisobutyl ketone, isophorone; dichloromethane, carbon tetrachloride, chloroform Halogenated hydrocarbon solvents such as chlorobenzene; dieth, chlor
  • the reaction temperature in step (1) is preferably ⁇ 78 to 25 ° C., more preferably ⁇ 20 to 10 ° C.
  • the reaction time in step (1) is preferably 0.5 to 24 hours, and more preferably 0.5 to 3 hours.
  • the above production method has the following general formula (C): (Wherein X is the same as above) and the following general formula (D): R 3 —OH (Wherein R 3 is the same as above), by reacting with the compound (D) represented by the formula (A), the step (2) of obtaining the compound (A) represented by the general formula (A) Further, it may be included.
  • step (2) can be carried out under known conditions.
  • the compound (A) obtained in the step (2) can be used for the reaction in the step (1).
  • the product after completion of each step, the product may be separated and purified by distilling off the solvent, distillation, column chromatography, recrystallization or the like.
  • Compound (1) is a novel compound and can be suitably used as various chemicals such as medical and agrochemical compounds, and intermediates thereof.
  • Example 1 ⁇ Synthesis of 2-propynyl (diethylcarbamoyl) fomate> 2-propynyl (chlorocarbonyl) fomate (1.47 g, 10 mmol) and 5 ml of dichloromethane were mixed and purged with nitrogen, and then diethylamine (0.73 g, 10 mmol) was added dropwise at 0 ° C. A solution obtained by mixing pyridine (0.87 g, 11 mmol) and 5 ml of dichloromethane was added dropwise to the solution. Then, it returned to room temperature and stirred. Celite filtration, washing with 1M aqueous hydrochloric acid solution, and liquid separation, followed by water washing and separation operation twice with water. The organic layer was dried and concentrated to obtain 1.20 g (GC purity: 98.3%) of the target compound represented by the following formula.
  • Example 2 ⁇ Synthesis of allyl (diethylcarbamoyl) formate> The synthesis was carried out with the same amount of substance as in Example 1 except that allyl (chlorocarbonyl) fomate was used instead of 2-propynyl (chlorocarbonyl) fomate, and 1.21 g of the desired product represented by the following formula (GC purity 96 .2%).
  • Example 3 Synthesis of 2-propynyl-2-morpholino-2-oxoacetate> The synthesis was carried out in the same amount of substance as in Example 1 except that morpholine was used instead of diethylamine to obtain 1.11 g (GC purity 98.0%) of the target compound represented by the following formula.
  • Example 4 Synthesis of 3- (trimethylsilyl) -2-propynyl (diethylcarbamoyl) fomate> Synthesis was carried out with the same amount of substance as in Example 1 except that 3- (trimethylsilyl) -2-propynyl (chlorocarbonyl) fomate was used instead of 2-propynyl (chlorocarbonyl) fomate. 1.30 g (GC purity 97.3%) was obtained.
  • Example 5 Synthesis of 2-propynyl (diallylcarbamoyl) fomate> The synthesis was performed with the same amount of substance as in Example 1 except that diallylamine was used in place of diethylamine to obtain 1.21 g of the target product represented by the following formula (GC purity 96.2%).
  • Example 6 Synthesis of 2-propynyl (di (2-propynyl) carbamoyl) fomate> The synthesis was carried out with the same amount of substance as in Example 1 except that di (2-propynyl) amine was used instead of diethylamine to obtain 1.09 g (GC purity 95.8%) of the target compound represented by the following formula. It was.
  • Example 7 Synthesis of 2-fluoroallyl (diallylcarbamoyl) fomate> The synthesis was carried out with the same amount of substance as in Example 5 except that 2-fluoroallyl (chlorocarbonyl) fomate was used instead of 2-propynyl (chlorocarbonyl) fomate, and 1.28 g of the desired product represented by the following formula ( GC purity 97.2%) was obtained.
  • Example 8 ⁇ Synthesis of allyl (diallylcarbamoyl) formate> The synthesis was carried out with the same amount of substance as in Example 5 except that allyl (chlorocarbonyl) fomate was used instead of 2-propynyl (chlorocarbonyl) fomate, and 1.20 g of the target compound represented by the following formula (GC purity 96 8%).
  • Example 9 ⁇ Synthesis of allyl (bis (2,2,2-trifluoroethyl) carbamoyl) fomate> The synthesis was carried out with the same amount of substance as in Example 2 except that bis (2,2,2-trifluoroethyl) amine was used instead of diallylamine, and 1.39 g of the desired product represented by the following formula (GC purity 96 8%).
  • Example 10 Synthesis of 2-fluoroallyl (diethylcarbamoyl) fomate> Synthesis was carried out with the same amount of substance as in Example 1 except that 2-fluoroallyl (chlorocarbonyl) fomate was used instead of 2-propynyl (chlorocarbonyl) fomate, and 1.22 g of the target compound represented by the following formula ( GC purity 96.8%) was obtained.
  • the compounds of the present disclosure can be used as various chemicals such as medical and agrochemical compounds, and intermediates thereof.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/JP2019/005765 2018-04-02 2019-02-18 化合物の製造方法及び化合物 WO2019193846A1 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018070741 2018-04-02
JP2018-070741 2018-04-02

Publications (1)

Publication Number Publication Date
WO2019193846A1 true WO2019193846A1 (ja) 2019-10-10

Family

ID=68100386

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/005765 WO2019193846A1 (ja) 2018-04-02 2019-02-18 化合物の製造方法及び化合物

Country Status (2)

Country Link
TW (1) TW201943688A (zh)
WO (1) WO2019193846A1 (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113363585A (zh) * 2021-07-23 2021-09-07 中节能万润股份有限公司 一种新型锂离子电池电解液添加剂及其应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1002318B (de) * 1954-04-17 1957-02-14 Heyden Chem Fab Verfahren zur Herstellung von bakteriostatisch wirksamen Oxamidsaeureestern
DE3312498A1 (de) * 1983-04-07 1984-10-11 Bayer Ag, 5090 Leverkusen Carbamidsaeureester
US4721523A (en) * 1984-09-13 1988-01-26 Bayer Aktiengesellschaft Herbicidal agents containing photosynthesis-inhibiting herbicides in combination with carbamate derivatives
JPH02142767A (ja) * 1988-07-15 1990-05-31 Basf Ag アゼチジン誘導体、これを含有する植物成長制御剤及びこれを使用する植物成長制御方法
US5385902A (en) * 1993-09-01 1995-01-31 Rohm And Haas Company Iodopropargylated oxalic derivatives as antimicrobial agents

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1002318B (de) * 1954-04-17 1957-02-14 Heyden Chem Fab Verfahren zur Herstellung von bakteriostatisch wirksamen Oxamidsaeureestern
DE3312498A1 (de) * 1983-04-07 1984-10-11 Bayer Ag, 5090 Leverkusen Carbamidsaeureester
US4721523A (en) * 1984-09-13 1988-01-26 Bayer Aktiengesellschaft Herbicidal agents containing photosynthesis-inhibiting herbicides in combination with carbamate derivatives
JPH02142767A (ja) * 1988-07-15 1990-05-31 Basf Ag アゼチジン誘導体、これを含有する植物成長制御剤及びこれを使用する植物成長制御方法
US5385902A (en) * 1993-09-01 1995-01-31 Rohm And Haas Company Iodopropargylated oxalic derivatives as antimicrobial agents

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
GEHANNE, SYLVIE: "Approaches to the Synthesis of 2-Sila-1-carba-cephalosporins", TETRAHEDRON LETTERS, vol. 35, no. 13, 1994, pages 2047 - 2048, XP055645085 *
MCCOMBIE, STUART W.: "Synthesis of 3-heterosubstituted isocephem and iso-oxacephem antibiotics", TETRAHEDRON LETTERS, vol. 27, no. 3, 1986, pages 305 - 308, XP055645072 *
NEVEUX, MURIEL: "Novel syntheses of oxamides, oxamates and oxalates from diisopropenyl oxalate", TETRAHEDRON, vol. 49, no. 13, 1993, pages 2629 - 2640, XP055645119 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113363585A (zh) * 2021-07-23 2021-09-07 中节能万润股份有限公司 一种新型锂离子电池电解液添加剂及其应用

Also Published As

Publication number Publication date
TW201943688A (zh) 2019-11-16

Similar Documents

Publication Publication Date Title
BRPI0914311A2 (pt) processo para preparação de promotor de apoptose abt-263
US20190084948A1 (en) Efficient and scalable synthesis of 2-(1'H-Indole-3'-Carbonyl)-thiazole-4-carboxylic acid methyl ester and its structural analogs
JP6923559B2 (ja) 芳香族フッ素化方法
Zhu et al. Synthesis of Fluoroalkyl Substituted Heterocycles Using Fluorinecontaining Building Blocks
JP2021165294A (ja) 新規スルファミン酸リチウム
AU2018397684B2 (en) Process for the preparation of an amino-pyrimidine and intermediates thereof
WO2019193846A1 (ja) 化合物の製造方法及び化合物
JP2001506254A (ja) チアゾール誘導体の製造方法
JPWO2019208807A1 (ja) 芳香族ニトリル化合物の製造方法
JPH08193076A (ja) Ｎ−アシル助剤を合成する方法
TW201139389A (en) Process for the preparation of 5-substituted 1-alkyltetrazoles
US20120029202A1 (en) Process for the Preparation of 5-Substituted 3-Aryl-3-(trifluoromethyl)-3,4-dihydro-2H-pyrroles
US4581466A (en) Process for the preparation of benzo-fused, tetrachlorinated heterocyclic compounds
JP2019094317A (ja) 化合物及び化合物の製造方法
JP3007610B2 (ja) シアノホルメートエステルの製造方法
JP4507398B2 (ja) ３−ハロメチルオキセタン化合物の合成方法
JP2013129616A (ja) 臭素化剤及びその利用
JP6347460B2 (ja) （トリハロメチル）ベンゼン誘導体及びその製造方法
JPH0625154B2 (ja) ベンズオキサゾリル−及びベンズチアゾリルオキシフエノキシプロピオン酸誘導体の製造法
WO2019001292A1 (zh) 4'-硫代核苷的新型化合物的制备方法和此制备方法中的中间体
KR20240097858A (ko) 특정 메소이온성 살충제의 제조 방법
JPS6230193B2 (zh)
KR20200116118A (ko) 2-클로로-4-니트로이미다졸 유도체의 제조 방법
KR20160059124A (ko) 헤테로고리계 발포제, 그 제조방법 및 이를 이용한 합성수지 발포방법
JP2016216405A (ja) ピリジン化合物の製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19781695

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19781695

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP