WO1999050231A1 - Procede de production de compose d'oxime - Google Patents

Procede de production de compose d'oxime Download PDF

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Publication number
WO1999050231A1
WO1999050231A1 PCT/JP1999/001522 JP9901522W WO9950231A1 WO 1999050231 A1 WO1999050231 A1 WO 1999050231A1 JP 9901522 W JP9901522 W JP 9901522W WO 9950231 A1 WO9950231 A1 WO 9950231A1
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WO
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Prior art keywords
group
compound
methyl
general formula
ketoester
Prior art date
Application number
PCT/JP1999/001522
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English (en)
Japanese (ja)
Inventor
Hiroshi Shimojitosho
Original Assignee
Shionogi & Co., Ltd.
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 Shionogi & Co., Ltd. filed Critical Shionogi & Co., Ltd.
Priority to JP2000541140A priority Critical patent/JP4416945B2/ja
Priority to AU29578/99A priority patent/AU2957899A/en
Publication of WO1999050231A1 publication Critical patent/WO1999050231A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds

Definitions

  • the present invention relates to a method for producing an oxic compound. Background technology
  • Oxim compounds are useful as intermediates in pesticides.
  • Japanese Unexamined Patent Publication No. Hei 3 — 2464268 discloses that 2-hydroxyminino 1-2-aryl acetate amide compound is used for agricultural purposes. It is used as an intermediate for synthesizing fungicides, and an alkoxy compound derived from the oxam compound exhibits a bactericidal action. This is stated.
  • This alkoxy compound has two kinds of isomers, E-form and Z-isomer, and almost all of them show a bactericidal action.
  • the oxime compound is easily retained in its steric configuration by an alkylating agent such as dimethyl sulfate or dimethyl sulfate.
  • an alkylating agent such as dimethyl sulfate or dimethyl sulfate.
  • the present invention has been developed from a dialkylester oxalate and an organic magnesium noride, and has undergone a series of processes.
  • the ⁇ -keto amide compound is produced from the compound at a high yield without the need for complicated separation operations, and the ⁇ -keto amide compound is then produced.
  • Kazura (() — Providing a method for producing a compound of high yield without the need for a complicated separation operation in a selective manner. Is an issue. Disclosure of the invention
  • the present inventors have made intensive studies from the viewpoint described above, and as a result, have found out from dialkyl ester oxalate and organic magnesium noride.
  • ⁇ dialkyl ester oxalate and organic magnesium noride.
  • the ⁇ -ketoester compound can be manufactured and then the ⁇ -ketoamide compound can be easily separated from the ⁇ -ketoamide compound without the need for complicated separation operations. , And then require a complicated separation operation to selectively select ⁇ -keto amide compounds from ( ⁇ ) -year-old kissm compounds.
  • the present invention is characterized by including the following steps (a) to (c): (ii) a method for producing an oxic compound; .
  • R 1 represents a straight-chain or branched alkyl group having 4 to 8 carbon atoms
  • a dialkyl oxalate ester represented by the following formula:
  • R 2 and R 3 are each independently a straight-chain or branched alkyl group having 1 to 8 carbon atoms, an alkyl group or a substituted alkyl group.
  • a substituted arylalkyl group or a hydrogen atom represented by a hydrogen atom is substituted with a straight-chain or branched alcohol having 4 to 8 carbon atoms. Is reacted as a solvent to obtain a compound represented by the general formula (5):
  • a straight-chain or branched alcohol having 4 to 8 carbon atoms is obtained by mixing the peak amide compound obtained in the step and hydroxylamine hydrochloride.
  • the reaction is carried out by using the solvent as a solvent, and the general formula (6):
  • Ar in the general formula (1) represents an aryl group or a substituted aryl group
  • X represents a chlorine atom, a bromine atom or Represents an iodine atom.
  • aryl group examples include phenyl group, naphthyl group, pyridyl group, and furyl group.
  • the number of substituents of the substituted aryl group is arbitrarily selected in the range of 1 to 5. However, the types may be the same or different.
  • Specific examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, and the like, a methyl group, a trifluoromethyl group, an ethyl group, and an n-butyl group.
  • organic magnesium halides (1) include, for example, phenylmagnesium chloride and phenylmagnesium chloride. ⁇ ⁇ 2 — ⁇ 2 — 2-— — — — ⁇ ⁇ 1 1 1 1 ⁇ — — ⁇ — Simum chloride, 2—Front opening magnesium chloride, 2—Cloom opening magnesium chloride, 3 — Trifluorene romyl phenyl magnesium bromide, 2 — methyl phenyl magnesium chloride, 4 milfinyl Enilele Magnesium chloride, 41 (t-butyl) phenyl Magnesium bromide, 2-methyxenil magnesium ⁇ M-chloride, 4-methoxyphenyl magnesium chloride, 2 — benzylylmagnesium chloride, 3 — ( 2 — Fluorobenzene) phenylmagnesium chloride, 4 — (41 (t-butylylene) benzylylene) phenylmagnet Sym
  • R 1 in the general formula (2) represents a straight-chain or branched alkyl group having 4 to 8 carbon atoms. Specific examples are as follows: 1-butyl group, 2—methyl-12-butyl group, 1—pentyl group, 2—pentyl group, 3—pentyl group, 2—methyl-11-butyl group, 3—methyl-11-butyl group, 1—hexylyl group, 2—hexyl group, 3—hexyl group, 2, 3 — dimethyl 1-butyl group, 3, 3 — dimethyl 1-butyl group, 2 — ethyl 1-butyryl group, 2 — methyl 1-2-pentyl group, 2-methyl-1-3-pentylyl group, 3-methyl 1-1-pentyl group, 3-methylyl 2-pentylyl group, 3 — Methyl 3 — Pentyl group, 4 — Methyl — 1 1 Pentyl group, 4 1 Methyl 1 2 — Penty
  • dialkyl oxalate (2) used is in the range of 1 to 2 equivalents of the organic magnesium halide (1) used. Can be selected arbitrarily.
  • Solvents used for the reaction include ether systems such as ethyl ether, tetrahydrofuran, and 1,2-dimethoxethane.
  • a solvent is used, and if necessary, a saturated aliphatic hydrocarbon compound such as n-hexane, n-heptane, n-octane, etc.
  • Aromatic hydrocarbon compounds such as benzene, toluene, and xylene are used as co-solvents in the range of 1 to 50% by weight of the ether-based solvent. used .
  • the amount of the solvent used can be arbitrarily selected within a range of 1 to 50 times the weight of the dialkyl oxalate ester (2).
  • the dripping temperature of the organic magnesium hydroxide (1) is arbitrarily selected within the range of 130 to 30 ° C, and if necessary, the reaction and mixing after the dripping
  • the product may be aged, its aging temperature is arbitrarily selected within the range of ⁇ 30 to 30 ° C, and the aging time is arbitrarily selected within the range of 1 to 10 hours.
  • the reaction is preferably performed in an inert gas atmosphere, such as nitrogen gas.
  • the post-treatment of the reaction is usually carried out by hydrolysis with normal acid, and the acid used in this case is an inorganic acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, or acetic acid.
  • Aqueous solutions of organic acids are used.
  • the concentration of the acid in the acid aqueous solution is arbitrarily selected in the range of 1 to 80% by weight.
  • the temperature during acid hydrolysis can be arbitrarily selected within the range of 0 to 80 ° C. I can.
  • the solvent is distilled off from the reaction mixture under normal or reduced pressure, and the concentrated residue is separated to obtain the desired ⁇ -ketoester.
  • the organic layer containing the compound (3) is separated.
  • the solvent used in the reaction (the ether-based solvent and, if necessary, the solvent used) is used.
  • the operation was stopped at the stage where the co-solvent was distilled off, and the alcohol by-product (alcohol having 4 to 8 carbon atoms represented by RioH) was distilled off.
  • the organic layer is separated and the organic layer is separated.
  • the ⁇ -ketoester compound (3), which is the target, is carbon number 4 to 8 It is preferable to obtain an alcohol solution of the above, and to use it as it is in the next step.
  • the organic layer obtained by the above-mentioned liquid separation operation may be subjected to distillation, silica gel chromatography, or the like, if necessary. Then, a purified product of the desired ⁇ -ketoester compound may be obtained, and the purified product may be used in the next step.
  • the ⁇ -ketoester compound (3) and the amide compound (4) are combined in a straight chain or branched alcohol having 4 to 8 carbon atoms. By reacting, the ketoamide compound (5) is obtained.
  • the ⁇ -ketoester compound (3) is usually dissolved in a linear or branched alcohol having 4 to 8 carbon atoms as a solution.
  • the alcohol solution it is preferable to use the organic layer obtained by the liquid separation operation in the step (a) as it is as the alcohol solution. If necessary, add a straight chain or branched alcohol having 4 to 8 carbon atoms.
  • An alcohol solution may be prepared.
  • R 2 and R 3 are each independently a carbon number:! Straight-chain or branched alkyl, benzyl, 2-phenylene, 11-phenylene, etc. Represents a alkyl group or a substituted alkyl group or a hydrogen atom. Specific examples of the alkyl group include a methyl group, an ethyl group,
  • substituent of the alkyl group include halogen atoms such as a fluorine atom, a chlorine atom, a methyl group, a trifluoromethyl group, Ethyl group, 1—propyl group, 2—propyl group, 1-butyl group, 2—butyl group, 2—methyl group, 1-propyl group, 2— Methyl 2 — unsubstituted or substituted alkyl, methoxy, ethoxy, and propyloxy groups such as propyl , 2 — Propoxy group, 1 — Butoxy group,
  • amide compound (4) include, for example, methylamine, ethylamine, n-propylamine, and i-propylamine.
  • a straight-chain or branched alcohol having 4 to 8 carbon atoms is used as the solvent used for the reaction. Specific examples are 1-butanol, 2—butanol, 2—methyl, 1—pentanol, 1—pentanol, and 2—pentol.
  • the amine compound (4) is dropped into an alcohol solution of the ⁇ -ketoester compound (3), and the dropping temperature at this time is 0. It can be arbitrarily selected within the range of ⁇ 50 ° C.
  • the temperature is arbitrarily selected in the range of 0 to 50 ° C and the time is arbitrarily selected in the range of 1 to 10 hours.
  • the reaction mixture After completion of the reaction, add acid to the reaction mixture, adjust the pH to 3 or less, and stir for a while.
  • an aqueous solution of hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, or the like is used, and its concentration is in a range of 1 to 80% by weight. It can be chosen arbitrarily.
  • the temperature during the stirring is arbitrarily selected within a range of 0 to 80 ° C, and the stirring time is within a range of 1 to 10 hours.
  • reaction mixture is separated, and the organic layer containing the desired ⁇ -ketoamide compound (5) is separated.
  • the organic layer obtained by separating the reaction mixture described above, that is, the ⁇ -ketoamide compound (5), which is the target It is preferable to use an alcohol solution having 4 to 8 carbon atoms as it is in the next step. If necessary, the organic layer obtained by the above-mentioned liquid separation operation may be subjected to distillation, silica gel caramuku mouth matography, etc., if necessary.
  • the purified ⁇ -keto amide compound (5) is obtained by subjecting it to a refined product which can be used in the next step.
  • the ⁇ -keto amide compound (5) is usually used as a solution obtained by dissolving the ⁇ -keto amide compound (5) in a linear or branched alcohol having 4 to 8 carbon atoms.
  • the alcohol solution it is preferable to use the organic layer obtained by the liquid separation operation in the step (b) as it is, and it is necessary to use the alcohol layer as it is. Straight or branched, if necessary, with 4 to 8 carbon atoms Add a call.
  • an alcohol solution may be prepared in this step. .
  • the solvent used is a straight-chain or branched alcohol having 4 to 8 carbon atoms, and a specific example thereof is (b) a step-wise ketamide. This is the same as that listed when manufacturing the compound (5).
  • a specific example thereof is (b) a step-wise ketamide. This is the same as that listed when manufacturing the compound (5).
  • the amount of the hydroxyalumine hydrochloride to be used can be arbitrarily selected within a range of 1 to 5 equivalents of the ⁇ -ketoamide compound 5).
  • the reaction temperature is arbitrarily selected in the range of 40 to 100 ° C, and the reaction time is arbitrarily selected in the range of 1 to 10 hours.
  • the reaction temperature is preferably set to 65 to 100 ° C from the viewpoint of increasing the production rate of the whole.
  • the temperature during cooling can be arbitrarily selected in the range of 0 to 30 ° C, and the cooling time can be arbitrarily selected in the range of 1 to 5 hours.
  • Solvents used for washing subsequent to washing with water include aryl alcohols such as methanol, ethanol, and disc mouth panels, and alcohol. Ketones such as tones and methyl ketones are used, and the used amount is washed and used. Arbitrarily selected within the range of 110 times
  • the drying of the product can be carried out arbitrarily within the range of 30 to 100 ° C. At the specified temperature, the process is performed under normal pressure or reduced pressure until the weight is no longer reduced.
  • Di-n-butyl oxalate was added to the flask at 20.23 g (0.100 mol) and tetrahydrofuran at 360 g (0.50 mol). 0 mo 1), and in a nitrogen atmosphere, 1. 26 g (0.1 mol of OOmol) and 2.43 g of magnesium metal were obtained under a nitrogen atmosphere. (0. 100 mol), a solution of phenylmagnesium chloride in tetrahydrofuran, 49.75 g, prepared from 0. It dropped at 10 ° C. After dropping, the mixture was stirred at 0 to 10 ° C for 1 hour, and then 40.87 g of 12% by weight sulfuric acid was dropped at a temperature not exceeding 20 ° C to hydrolyze. did .
  • the (E) -oxo compound was identified by iH-NMR spectrum data.
  • the purity of the obtained (E) -oxo compound was 96%, and it contained 4% of the (Z) -isomer.
  • the (E) -oxo compound was identified by overnight ⁇ H-NMR spectrum analysis.
  • the (E) -oxo compound was identified by iH-NMR spectrum data.
  • Example 1 was repeated except that chlorobenzene was used instead of chlorobenzen ⁇ 4 2 6 (0100m ⁇ 1).
  • the (E) -oxo compound was identified from the NMR Sektorille de overnight.
  • Di-n-butyrate oxalate is added to the flask in the amount of 0.23 g (0.10 Omol), and the tetrahydrofuran in the form of 3.66 g (0.
  • composition of the reaction solution obtained by the reaction of the ⁇ -keto amide compound with hydroxylamin hydrochloride is in proportion to the solid content. Then, (E)-95% by weight of a simulated compound, (Z)-2% by weight of an oxime body, a-2% by weight of a ketoamide compound, And 1% by weight.
  • di-n-octyl oxalate 31.45 g (0.1 OO mol)
  • the (E) -oxo compound was identified by iH-NMR spectrum data.
  • Example 1 2-Instead of chlorodiphenyl badly, 2-kuroguchi 4 '-methyl diphenyl territol 21.887 g (0. Except that 100 m 0 1) was used, (E) a one-year-old kissm compound was produced in the same manner as in Example 7.
  • This ⁇ -ketoester compound is dissolved in 200 ml of methanol, and a 40 wt% aqueous solution of methylamine is obtained. g (0.210mo1) was added dropwise at room temperature and stirred overnight. The reaction mixture is concentrated under reduced pressure, and the residue is extracted with 300 ml of methyl ether, washed with 100 ml of water, and then washed with an organic layer. Was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, the residue was separated and purified by silica gel chromatography, and the ⁇ -ketoamide compound (8) was purified.
  • the ⁇ -ketoamide compound was dissolved in 100 ml of methanol, and 6.95 g of hydroxylaminate hydrochloride (0.1 Omo 1 ) And reacted for 4 hours at the reflux temperature. 500 ml of water was added to the reaction mixture, and extraction was carried out twice with 100 ml of ethyl ether. The organic layer was washed with 500 ml of water, and dried over anhydrous sodium sulfate.
  • This ⁇ -ketoester compound was dissolved in 200 ml of methanol, and a 40 wt% aqueous solution of methylamine was dissolved in 16.30 g ( 0.2 1 O mo 1) was added dropwise at room temperature, and the mixture was stirred overnight.
  • This ⁇ -keto amide compound is dissolved in 100 ml of methanol, and 6.95 g (0.1 OO mol) of hydroxylene amine hydrochloride is added. Added and reacted at reflux temperature for 4 hours. 500 ml of water was added to the reaction mixture, and the mixture was extracted twice with 500 ml of ethyl ether. The organic layer was washed with 500 ml of water, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from methanol.
  • the obtained (E) -year-old kimchi compound had a melting point of 83-86 ° C, a purity of 95%, and contained 5% of the (Z) -isomer.
  • Table 1 shows the above results.
  • dialkyl oxalate ester and organic magnesium eight-lead force are used. After departure, it went through a series of processes.
  • ⁇ -ketoester compounds can be produced at a high yield without the need for complicated separation operations for rachiketamido compounds.
  • the ⁇ -ketoamide compound can be used to increase the yield without the need for a complicated and selective separation of the oxime compound. It can be manufactured.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production efficace d'un composé de (E)-oxime à partir d'un oxalate de dialkyle et d'un halogénure organomagnésien, sans qu'une opération de séparation compliquée soit nécessaire. Ledit procédé se caractérise par : (a) la mise en réaction d'un halogénure organomagnésien représenté par la formule générale (1) ArMgX, avec un oxalate de dialkyle représenté par la formule générale (2) (CO2R1)2 (dans laquelle R1 représente alkyle C¿4?-8), de sorte qu'un composé α-cétoester représenté par la formule générale (3) soit produit; (b) la mise en réaction du composé α-cétoester résultant avec un composé aminé représenté par la formule générale (4) R?2R3¿NH, dans un alcool C¿4?-C8 utilisé comme un solvant, de manière qu'un composé α-cétoamide représenté par la formule générale (5) soit produit ; et (c) la mise en réaction du composé cétoamide résultant avec de l'hydrochlorure d'hydroxylamine dans un alcool C4-C8 utilisé comme solvant, de manière que le composé (e)-oxime cible représenté par la formule générale (6) soit produit.
PCT/JP1999/001522 1998-03-26 1999-03-25 Procede de production de compose d'oxime WO1999050231A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2000541140A JP4416945B2 (ja) 1998-03-26 1999-03-25 オキシム化合物の製造法
AU29578/99A AU2957899A (en) 1998-03-26 1999-03-25 Process for producing oxime compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP7933598 1998-03-26
JP10/79335 1998-03-26

Publications (1)

Publication Number Publication Date
WO1999050231A1 true WO1999050231A1 (fr) 1999-10-07

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011161076A1 (fr) 2010-06-22 2011-12-29 Bayer Cropscience Ag Procédé de préparation de dérivés de 1-alkyltétrazolyl-oxime substitués en position 5

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104610091B (zh) * 2015-02-05 2016-09-21 北京颖泰嘉和生物科技股份有限公司 一种提纯n-甲基苯甲酰甲酰胺粗品的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06219986A (ja) * 1992-11-02 1994-08-09 Shionogi & Co Ltd （ｅ）−アルコキシイミノまたはヒドロキシイミノアセトアミド系化合物の製造法およびその製造用中間体
JPH10501248A (ja) * 1994-06-10 1998-02-03 ビーエーエスエフ アクチェンゲゼルシャフト α−メトキシイミノカルボン酸メチルアミドの製造方法およびその中間生成物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06219986A (ja) * 1992-11-02 1994-08-09 Shionogi & Co Ltd （ｅ）−アルコキシイミノまたはヒドロキシイミノアセトアミド系化合物の製造法およびその製造用中間体
JPH10501248A (ja) * 1994-06-10 1998-02-03 ビーエーエスエフ アクチェンゲゼルシャフト α−メトキシイミノカルボン酸メチルアミドの製造方法およびその中間生成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011161076A1 (fr) 2010-06-22 2011-12-29 Bayer Cropscience Ag Procédé de préparation de dérivés de 1-alkyltétrazolyl-oxime substitués en position 5

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AU2957899A (en) 1999-10-18

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