WO2001090058A1 - Composes de nitrile et procede de preparation correspondant - Google Patents

Composes de nitrile et procede de preparation correspondant Download PDF

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Publication number
WO2001090058A1
WO2001090058A1 PCT/JP2001/004329 JP0104329W WO0190058A1 WO 2001090058 A1 WO2001090058 A1 WO 2001090058A1 JP 0104329 W JP0104329 W JP 0104329W WO 0190058 A1 WO0190058 A1 WO 0190058A1
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WO
WIPO (PCT)
Prior art keywords
alkyl group
independently represent
equation
formula
compound represented
Prior art date
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PCT/JP2001/004329
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English (en)
Japanese (ja)
Inventor
Kenzo Fukuda
Yasuo Kondo
Tadashi Ohtsu
Original Assignee
Nissan Chemical Industries, 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.)
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Publication date
Application filed by Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to AU2001260607A priority Critical patent/AU2001260607A1/en
Publication of WO2001090058A1 publication Critical patent/WO2001090058A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

Definitions

  • the present invention relates to a 3- (4-cyanophenyl) peracyl derivative useful as a herbicide or an intermediate thereof (described in US Pat. No. 5,127,935 and Japanese Patent Application Laid-Open No. 5-1866436).
  • the present invention relates to a method for producing a nitrile compound which is an important intermediate of the above. Background art
  • Japanese Patent Application Laid-Open No. 9-48771 describes a method of cyanating a 3- (4-halogenophenyl) peracyl derivative with copper cyanide. ing.
  • An object of the present invention is to provide an industrially advantageous method for producing a nitrile compound. Disclosure of the invention
  • the present inventors have conducted intensive studies to solve the above-mentioned problems.
  • the benzene compound is formylated to form an aldehyde compound, a dihydroquinazoline compound or a mixture thereof, and then the oxime is formed and dehydrated, whereby the important intermediate is obtained. It has been found that a nitrile compound can be produced at a low cost by an easy operation, and the present invention has been achieved.
  • R 1 and R 2 each independently represent a Ci-Cs alkyl group.
  • R 1 and R 2 each independently represent a Ci-Ce alkyl group.
  • R 1 and R 2 each independently represent a Ci-C 6 alkyl group.
  • R 1 and R 2 each independently represent a Ci-Cs alkyl group. Represented by Aldehyde compound of the formula (4)
  • R 1 and R 2 each independently represent a C i -C 6 alkyl group.
  • R 1 and R 2 each independently represent a C] -C 6 alkyl group.
  • R 1 and R 2 each independently represent a C i -Cs alkyl group.
  • R 1 and R 2 each independently represent a Ci-Ce alkyl group.
  • R 1 and R 2 each independently represent a Ci-Ce alkyl group.
  • R 1 and: 2 each independently represent a C i -Cs alkyl group.
  • R 1 and R 2 each independently represent a Ci-C 6 alkyl group.
  • R and R 2 each independently represent a C i -C 6 alkyl group.
  • R 1 and R 2 each independently represent a C i -Cs alkyl group.
  • R 1 and R 2 each independently represent a Ci-Cs alkyl group.
  • R 1 and R 2 each independently represent a Ci-Cs alkyl group.
  • R 1 and R 2 each independently represent a Ci-C 6 alkyl group.
  • R 1 and R 2 each independently represent a C i -C 6 alkyl group.
  • R 1 and R 2 are preferably a normal butyl group, a secondary butyl group, a tertiary butyl group, a propyl group, a isopropyl group And an ethyl group and a methyl group, more preferably a methyl group and an ethyl group.
  • the benzene compound represented by the formula (5) which is a starting material of the present invention, is produced, for example, by the method described in Japanese Patent Publication No. JP-P5-4959.
  • Acid catalysts include inorganic substances such as trifluoroacetic acid, paratoluenesulfonic acid, methanesulfonic acid, acetic acid, formic acid, sulfuric acid, sulfuric acid, hydrochloric acid, hydrogen chloride gas, hydrobromic acid, hydrogen bromide gas, and hydroiodic acid.
  • Organic acidic compounds can be used alone or as a mixture.
  • the product is present in the form of an aldehyde compound, a dihydroquinazoline compound or a mixture thereof depending on conditions, but the mixture can be subjected to the next reaction as it is.
  • the reagents and reaction conditions used for converting the aldehyde compound, the dihydroquinazoline compound or a mixture thereof into the oxime compound are as follows, but are not limited thereto.
  • Hydroxylamine or hydroxylamine The compound is hydroxylamine or an aqueous solution thereof, or an inorganic salt or an organic salt such as a hydrochloride, a sulfate, a nitrate, or a phosphate. It is from 0.8 to 2 equivalents, preferably from 1.0 to 1.2 equivalents, based on the mixture.
  • an inorganic basic compound such as sodium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium acetate, or a neutralizing agent such as amine or pyridine is used as a neutralizing agent.
  • Organic basic compounds can also be added.
  • the reagents and reaction conditions used when converting the oxime compound to the nitrile compound are as follows, but are not limited thereto. Trifluoroacetic acid, paratoluenesulfonic acid, methanesulfonic acid, acetic acid, sulfuric acid, sulfuric acid, sulfuric acid, hydrochloric acid, hydrogen chloride gas, hydrobromic acid, hydrobromic acid, hydrogen chloride gas, iodine, which can be generally used for a dehydration reaction as a reaction reagent
  • acidic substances such as hydrofluoric acid, acetic acid, formic acid, etc., thionyloxy chloride salt, pentachloride, ⁇ , ⁇ '-carbonyldiimidazole, ⁇ , ⁇ '-dicyclohexylcarbodiimid Reagents with high reactivity with water such as pentane, ichlic acid pentate, acetic anhydride, trifluoroacetic anhydride, and t
  • a solvent can be used.
  • the solvent may be any solvent that does not react with the reagents used.
  • benzene solvents such as benzene, toluene, chlorobenzene, dichlorobenzene, etc.
  • ester solvents such as ethyl acetate and butyl acetate, and 1, 2 —
  • halogenated solvents such as dichloroethane
  • amides such as ⁇ , ⁇ -dimethylformamide, ⁇ , ⁇ ⁇ ⁇ ⁇ -dimethylacetamide
  • cyclic amides such as 1-methyl-2-pyrrolidinone, tetramethylperylene, Aprotic polar solvents such as tetraureas such as tetraethyl perrea; cyclic ureas such as 1,3-dimethyl-2-imidazolidinone
  • ethers such as ethylene glycol dimethyl ether and diethylene glycol dimethyl
  • the amount of the solvent used is usually in the range of 1 to 20 times the amount of the starting benzene compound. It is preferably in the range of 3 to 10 times.
  • the double amount is based on the weight. For example, a 20-fold amount means 20 times the weight.
  • Any of the above reactions can be carried out at a low temperature, a high temperature, or a high pressure, but is preferably from 110 ° C under normal pressure to the boiling point of the solvent used.
  • the oxime compound or nitrile compound can be obtained without isolating the intermediate from the benzene compound by continuously or mixedly introducing the reagents using the same solvent. Can also be simplified.
  • reaction solution was cooled, 30 g of 5% hydrochloric acid was added at 30 ° C or lower, and the organic layer was separated.
  • the aqueous layer was adjusted to pH 7 with a 10% aqueous sodium hydroxide solution, and the precipitated crystals were filtered.
  • 5-1-ethanesulfonylamino-2-fluoro-41-formylphenyl) ethyl carbenomate mp 188.8 ° C
  • (1-ethanesulfonyl-6-fluoro) 1,2-Dihydroquinazoline-17-yl) 27.2 g of a mixture of carpa and ethyl mitinate was obtained.
  • a mixture of 10.0 g of a mixture with ethyl ester of rubamic acid and 50.0 g of benzene is heated to 50 ° C and heated to 50 ° C to obtain 4.00 g of a 50% aqueous hydroxylamine solution (0.04 g). (0594 mol) was allowed to react for 2 hours.
  • a 200 ml reaction flask was charged with 5.0 g (0.0344 mol) of (5-ethanesulfonylamino-2-fluorophenyl) ethyl rubmate and 50 g of trifluoroacetic acid, and 4.88 g of hexamethylenetetramine. (0.0344 mol) was added at 30 ° C or less, and the reaction was allowed to proceed for 10 hours. Then, the temperature was raised to 6 Ot, and the reaction was further performed for 3 hours. Then, 6.89 g (0.0688 mol) of 98% sulfuric acid was added.
  • Example 4 The 5-ethanesulfonylamino obtained in Example 4 was placed in a 200 ml reaction flask.
  • a nitrile compound as an intermediate of a herbicide can be obtained at a low cost by an easy operation.

Abstract

Cette invention se rapporte à des composés de nitrile utiles comme intermédiaires dans la production d'herbicides, et à un procédé de préparation de ces composés. Ce procédé consiste à faire réagir un composé de benzène, représenté par la formule générale (1) (où R1 et R2 représentent chacun séparément alkyle C¿1?-C6) avec de l'hexaméthylèntétramine et un catalyseur acide, puis avec de l'hydroxylamine, et à soumettre ensuite le composé ainsi obtenu à une déshydratation, pour produire un composé de nitrile représenté par la formule (2) (où R?1 et R2¿ représentent chacun séparément alkyle C¿1?-C6).
PCT/JP2001/004329 2000-05-24 2001-05-23 Composes de nitrile et procede de preparation correspondant WO2001090058A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001260607A AU2001260607A1 (en) 2000-05-24 2001-05-23 Nitrile compounds and process for their preparation

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2000153655 2000-05-24
JP2000315119 2000-10-16
JP2000-315119 2000-10-16
JP2000-153655 2000-10-16

Publications (1)

Publication Number Publication Date
WO2001090058A1 true WO2001090058A1 (fr) 2001-11-29

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AU (1) AU2001260607A1 (fr)
WO (1) WO2001090058A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103113249A (zh) * 2013-03-05 2013-05-22 上虞盛晖化工有限公司 一种3-氨基-4,4,4-三氟丁烯酸乙酯的合成方法
CN110418792A (zh) * 2017-03-14 2019-11-05 第一三共株式会社 制备3,6-二取代咪唑并[1,2-b]哒嗪衍生物的方法
CN113880823A (zh) * 2020-07-02 2022-01-04 沈阳中化农药化工研发有限公司 一种制备含异噁唑啉脲嘧啶类化合物中间体的方法
RU2818999C1 (ru) * 2020-07-02 2024-05-08 Шэньян Сайнокем Агрокемикалз Р Энд Д Ко., Лтд. Способ получения интермедиата урацилового соединения, содержащего изоксазолин

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0496595A1 (fr) * 1991-01-23 1992-07-29 Nissan Chemical Industries, Limited Dérivés d'aniline et procédé pour leur préparation
EP0563384A1 (fr) * 1990-12-17 1993-10-06 Nissan Chemical Industries, Limited Derive d'uracile
JPH0948761A (ja) * 1995-08-07 1997-02-18 Nissan Chem Ind Ltd ３−（４−シアノフェニル）ウラシル誘導体の製造法
WO1998028280A1 (fr) * 1996-12-23 1998-07-02 Fmc Corporation Certains derives de 3-[2,4 disubstituee-5-(substituee amino)phenyle]-1-substituee-6-trifluorure-2,4-(1h,3h)-pyrimidinedione utilises en tant qu'herbicides
JPH10218862A (ja) * 1997-02-12 1998-08-18 Nissan Chem Ind Ltd ウラシル誘導体の製造方法
WO1999035122A1 (fr) * 1998-01-09 1999-07-15 Bayer Aktiengesellschaft Procede de fabrication de n-(3-amino-4-fluoro-phenyl) sulfonamides, de n-(3-amino-4-fluoro-phenyl) carbonamides et de n-(3-amino-4-fluoro-phenyl) carbamates
DE19962932A1 (de) * 1999-12-24 2001-06-28 Bayer Ag Verfahren zur Herstellung von N-substituierten 2,4-Diamino-5-fluor-benzonitrilen und neue Zwischenprodukte

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0563384A1 (fr) * 1990-12-17 1993-10-06 Nissan Chemical Industries, Limited Derive d'uracile
EP0496595A1 (fr) * 1991-01-23 1992-07-29 Nissan Chemical Industries, Limited Dérivés d'aniline et procédé pour leur préparation
JPH0948761A (ja) * 1995-08-07 1997-02-18 Nissan Chem Ind Ltd ３−（４−シアノフェニル）ウラシル誘導体の製造法
WO1998028280A1 (fr) * 1996-12-23 1998-07-02 Fmc Corporation Certains derives de 3-[2,4 disubstituee-5-(substituee amino)phenyle]-1-substituee-6-trifluorure-2,4-(1h,3h)-pyrimidinedione utilises en tant qu'herbicides
JPH10218862A (ja) * 1997-02-12 1998-08-18 Nissan Chem Ind Ltd ウラシル誘導体の製造方法
WO1999035122A1 (fr) * 1998-01-09 1999-07-15 Bayer Aktiengesellschaft Procede de fabrication de n-(3-amino-4-fluoro-phenyl) sulfonamides, de n-(3-amino-4-fluoro-phenyl) carbonamides et de n-(3-amino-4-fluoro-phenyl) carbamates
DE19962932A1 (de) * 1999-12-24 2001-06-28 Bayer Ag Verfahren zur Herstellung von N-substituierten 2,4-Diamino-5-fluor-benzonitrilen und neue Zwischenprodukte

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103113249A (zh) * 2013-03-05 2013-05-22 上虞盛晖化工有限公司 一种3-氨基-4,4,4-三氟丁烯酸乙酯的合成方法
CN103113249B (zh) * 2013-03-05 2015-06-03 上虞盛晖化工股份有限公司 一种3-氨基-4,4,4-三氟丁烯酸乙酯的合成方法
CN110418792A (zh) * 2017-03-14 2019-11-05 第一三共株式会社 制备3,6-二取代咪唑并[1,2-b]哒嗪衍生物的方法
US11667642B2 (en) 2017-03-14 2023-06-06 Daiichi Sankyo Company, Limited Method for producing 3,6-disubstituted-imidazo[1,2-b]pyridazine derivative
CN113880823A (zh) * 2020-07-02 2022-01-04 沈阳中化农药化工研发有限公司 一种制备含异噁唑啉脲嘧啶类化合物中间体的方法
WO2022002117A1 (fr) * 2020-07-02 2022-01-06 沈阳中化农药化工研发有限公司 Procédé de préparation de composés intermédiaires d'uracile contenant de l'isoxazoline
CN113880823B (zh) * 2020-07-02 2023-12-12 沈阳中化农药化工研发有限公司 一种制备含异噁唑啉脲嘧啶类化合物中间体的方法
RU2818999C1 (ru) * 2020-07-02 2024-05-08 Шэньян Сайнокем Агрокемикалз Р Энд Д Ко., Лтд. Способ получения интермедиата урацилового соединения, содержащего изоксазолин

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