EP3997075A1 - Procédé de fabrication de 2-(phénylimino)-1,3-thiazolidine-4-ones - Google Patents

Procédé de fabrication de 2-(phénylimino)-1,3-thiazolidine-4-ones

Info

Publication number
EP3997075A1
EP3997075A1 EP20735624.7A EP20735624A EP3997075A1 EP 3997075 A1 EP3997075 A1 EP 3997075A1 EP 20735624 A EP20735624 A EP 20735624A EP 3997075 A1 EP3997075 A1 EP 3997075A1
Authority
EP
European Patent Office
Prior art keywords
formula
alkyl
chlorine
methyl
carbonate
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
EP20735624.7A
Other languages
German (de)
English (en)
Inventor
Thomas Himmler
Julia Johanna HAHN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of EP3997075A1 publication Critical patent/EP3997075A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/54—Nitrogen and either oxygen or sulfur atoms

Definitions

  • the present invention relates to a process for the preparation of 2- (phenylimino) -l, 3-thiazolidin-4-ones of the general formula (I).
  • 2- (Phenylimino) -l, 3-thiazolidin-4-ones and corresponding derivatives are of great importance in the pharmaceutical and agrochemical industry as intermediates for the production of, for example, chiral sulfoxides.
  • Such sulfoxides are used, for example, in crop protection as acaricidal agents (see, for example, WO2013 / 092350 or WO2015 / 150348).
  • a process that has become known for the preparation of 2- (phenylimino) -l, 3-thiazolidin-4-ones of the general formula (I) is accordingly characterized in that an aniline of the general formula (IV) is mixed with an isothiocyanate in a first step of the general formula (V) or an aryl isothiocyanate of the general formula (VI) is reacted with an amine of the general formula (VII) and then the thiourea of the general formula (II) thus formed is isolated, for example by filtration.
  • the thiourea of the general formula (II) is then combined with an acetic acid derivative of the general formula (III) in the presence of a base to give 2- (phenylimino) -l, 3-thiazolidin-4-one of the general formula ( I) implemented.
  • 2- (phenylimino) -l, 3-thiazolidin-4-ones of the general formula (I) can be prepared by adding an aniline of the general formula (IV) in the presence of an acetic acid derivative of the general formula (III) and a base is reacted with an isothiocyanate of the general formula (V), the thiourea of the general formula (II) formed as an intermediate reacting directly and preferably in situ to give the 2- (phenylimino) -l, 3-thiazolidin-4-one.
  • the present invention accordingly provides a process for the preparation of 2- (phenylimino) - l, 3-thiazolidin-4-ones of the general formula (I) in which
  • Y 1 and Y 2 independently represent fluorine, chlorine or hydrogen
  • R 1 and R 2 independently represent hydrogen, (Ci-Ci 2 ) alkyl, (Ci-Ci 2 ) haloalkyl, cyano, halogen or nitro, and
  • R 3 represents optionally substituted (Ce-Cio) aryl, (Ci-Ci 2 ) alkyl or (Ci-Ci 2 ) haloalkyl, the substituents being selected from halogen, (Ci-C 6 ) alkyl, (C 3 -Cio ) Cycloalkyl, cyano, nitro, hydroxy, (Ci-C 6 ) alkoxy, (Ci-C 6 ) haloalkyl and (Ci-C 6 ) haloalkoxy, in particular from fluorine, chlorine, (Ci-C 3 ) alkyl, (C 3 -C 6 ) Cycloalkyl, cyclopropyl, cyano, (Ci-C 3 ) alkoxy, (Ci-C 3 ) haloalkyl and (Ci-C 3 ) haloalkoxy, which is characterized in that an aniline of the formula (IV)
  • X stands for bromine, chlorine, OSCFMe, OSCFPh, 0S0 2 (4-Me-Ph) or OSO2CF3, and
  • W is OH or a radical 0 (Ci -Ce-alkyl), and in the presence of a base with an isothiocyanate of the formula (V)
  • R 3 has the meaning given above, initially to a thiourea of the formula (II)
  • the acetic acid derivative of the formula (III) is therefore already present when the aniline of the formula (IV) reacts with the isothiocyanate of the formula (V) to form the thiourea of the formula (II). It does not affect this reaction negatively and rather has the effect that the thiourea of the formula (II) does not accumulate in the reaction mixture, but is directly further converted to the compound of the formula (I). Consequently, the thiourea of the formula (II) is converted directly in situ the compound of the formula (I) reacted, ie the intermediately formed thiourea of the formula (II) reacts in situ directly further to give 2- (phenylimino) -1, 3-thiazolidin-4-one of the formula (I).
  • the compounds of the formula (I) can exist as E or Z isomers or as a mixture of these isomers. This is illustrated by the crossed double bond in formula (I).
  • the E isomer is present in each case.
  • the Z isomer is present in each case.
  • the Z isomer or a mixture of E and Z isomer is present in which the proportion of the Z isomer is greater than 50% and increasingly preferably greater than 60%, 65%, 70% , 75%, 80%, 85%, 90%, 95% based on the total amount of E and Z isomers in the mixture.
  • Y 1 and Y 2 independently of one another represent fluorine, chlorine or hydrogen
  • R 1 and R 2 independently of one another represent fluorine, chlorine (Ci-C3) alkyl or hydrogen, and
  • R 3 for optionally substituted phenyl, (Ci-C 6 ) AIkyI or (Ci-C 6 ) HalogenaIkyI, the substituents being selected from halogen, (Ci-C 6 ) AIkyI, (C3-Cio) CycIoaIkyI, cyano, nitro, Hydroxy, (Ci-C 6 ) alkoxy, (Ci-C 6 ) HalogenaIkyI and (Ci-C 6 ) HalogenaIkoxy, in particular from fluorine, chlorine, (Ci- C3) alkyl, (C3-C6) CycIoaIkyI, Cyclopropyl, Cyano, (Ci-C3) alkoxy, (Ci-C3) HalogenaIkyI and (Ci- C3) haloalkoxy.
  • Y 1 and Y 2 independently of one another represent fluorine or hydrogen
  • R 1 and R 2 independently of one another for fluorine, chlorine, hydrogen or methyl, and R 3 for (Ci-C ö j-alkyl or (Ci-C 6 ) HalogenaIkyI.
  • R 1 and R 2 independently of one another for fluorine, hydrogen or methyl, and R 3 for (Ci-C 6 ) haloalkyl.
  • X stand out for bromine or chlorine
  • R 2 for fluorine
  • R 3 for CH2CF3.
  • the 2- (phenylimino) -l, 3-thiazolidin-4-ones of the formula (I) can be prepared with good yields and in high purity using the process according to the invention.
  • the fact that in the process according to the invention the reaction of the aniline of the formula (IV) with the isothiocyanate of the formula (V) in the presence of a base and the acetic acid derivative of the formula (III) can be carried out with high selectivity and yield is surprising because it is known that anilines can be alkylated on nitrogen with acetic acid derivatives of the formula (III) (see for example US20050020645; WO2004 / 039764).
  • the process according to the invention allows the use of diluents suitable for the industrial scale, especially those in which voluminous precipitations of the thioureas of the formula (II) can otherwise occur.
  • Another resulting benefit for the Process economy is that the process according to the invention enables the desired target compounds to be obtained without the need for complex isolation processes for the intermediate stage.
  • Scheme (2) illustrates the pure implementation.
  • the compound of the formula (III) is present in the reaction mixture before at least one of the compounds of the formulas (IV) and (V) is added to the reaction mixture.
  • halogens includes elements selected from the group consisting of fluorine, chlorine, bromine and iodine, fluorine, chlorine and bromine being preferred and fluorine and chlorine being particularly preferred are preferred.
  • Optionally substituted groups can be monosubstituted or polysubstituted, and in the case of polysubstitutions the substituents can be identical or different.
  • the substituents are selected from halogen, (CVO,) alkyl, (C3- Cio) cycloalkyl, cyano, nitro, hydroxy, (CVOjAlkoxy, (C 1 -O,) halogenalkyl and (Ci - OjHalogenalkoxy, in particular from fluorine, chlorine, (Ci-C3) alkyl, (C3-C6) cycloalkyl, cyclopropyl, cyano, (Ci-C3) alkoxy, (Ci-C3) haloalkyl and (Ci-C3) haloalkoxy.
  • Alkyl groups substituted by one or more halogen atoms are selected, for example, from trifluoromethyl (CF 3 ), difluoromethyl (CHF 2 ), CF 3 CH 2 , CICH 2 , CF 3 CCI 2 .
  • alkyl groups are linear, branched or ring-shaped saturated hydrocarbon groups.
  • Ci-Ci2-alkyl comprises the largest range defined herein for an alkyl group.
  • this definition includes, for example, the meanings methyl, ethyl, n-, iso-propyl, n-, iso-, sec- and t-butyl, n-pentyl, n-hexyl, 1,3-dimethylbutyl, 3,3- Dimethylbutyl, n-heptyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl.
  • aryl groups are aromatic hydrocarbon groups which can have one, two or more heteroatoms (selected from O, N, P and S).
  • this definition includes, for example, the meanings cyclopentadienyl, phenyl, cycloheptatrienyl, cyclooctatetraenyl, naphthyl and anthracenyl; 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5- isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol- 3-yl, l, 2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl
  • the conversion of the aniline of the formula (IV) to the compound of the formula (I) is preferably carried out in the presence of a diluent.
  • a diluent of the invention Tetrahydrofuran (THF), dioxane, diethyl ether, methyl tert-butyl ether (MTBE), tert-amyl methyl ether (TAME), 2-methyl-THF, acetonitrile (ACN), acetone, butyronitrile, ethyl acetate, isopropyl acetate, butyl acetate, Pentyl acetate, methyl isobutyl ketone, ethylene carbonate, propylene carbonate, N, N-dimethylacetamide (DMAc), N, N-dimethylformamide (DMF), N-methylpyrrolidone, dimethyl sulfoxide (DMSO), sulfolane, tetrachlor
  • Preferred diluents for the process according to the invention are methylene chloride, chloroform, 1,2-dichloroethane, acetonitrile, acetone, ethyl acetate, methyl tert-butyl ether (MTBE), tetrahydrofuran (THF), 2-methyl-THF, N, N-dimethylacetamide (DMAc), N, N -Dimethylformamide (DMF), toluene, ortho-xylene, meta-xylene, para-xylene, ethylbenzene, mesitylene, chlorobenzene, 1,2-dichlorobenzene, anisole, n-heptane, n-octane, 1,2,4-trimethylpentane ( Isooctane), petroleum ether 40/55, special petrol 80/110, methylcyclohexane or mixtures of these diluents.
  • Particularly preferred diluents are acetonitrile, ethyl acetate, tetrahydrofuran (THF), toluene, ortho-xylene, meta-xylene, para-xylene, ethylbenzene, mesitylene, chlorobenzene, 1,2-dichlorobenzene, anisole, n-heptane, 1,2,4 -Trimethylpentane (isooctane), petroleum ether 40/55, special petrol 80/110, methylcyclohexane or mixtures of these diluents.
  • Toluene is very particularly preferred. ortho-xylene, meta-xylene, para-xylene, ethylbenzene or chlorobenzene or mixtures of these diluents.
  • the isothiocyanate of the formula (V) is preferably used in a molar quantitative ratio of 0.95: 1 to 2: 1, based on the aniline of the formula (IV). More preferred are quantitative ratios of 1.01: 1 to 1.5: 1, again based in each case on the aniline of the formula (IV).
  • Organic and inorganic bases can be used as the base in the process according to the invention.
  • organic bases that may be mentioned are trimethylamine, triethylamine, tributylamine and ethyldiisopropylamine.
  • inorganic bases are potassium acetate, sodium acetate, lithium hydroxide, potassium hydroxide, sodium hydroxide, potassium hydrogen carbonate, sodium hydrogen carbonate, potassium carbonate, sodium carbonate, cesium carbonate, calcium carbonate and magnesium carbonate. Potassium hydroxide, sodium hydroxide, potassium carbonate and sodium carbonate are preferred. Potassium carbonate is particularly preferred.
  • the base is preferably used in a molar quantitative ratio of 0.8: 1 to 3: 1, based on the aniline of the formula (IV). Quantitative ratios of 1: 1 to 2: 1 are further preferred, again based on the aniline of the formula (IV).
  • the acetic acid derivative of the formula (III) is preferably used in a molar quantitative ratio of 0.9: 1 to 2: 1, based on the aniline of the formula (IV). More preferred are quantitative ratios of 1.0: 1 to 1.5: 1, again based in each case on the aniline of the formula (IV).
  • the process according to the invention is generally carried out at a temperature between -20 ° C. and 150 ° C., preferably between 0 ° C. and 120 ° C., very particularly preferably between 5 ° C. and 80 ° C.
  • the reaction is typically carried out under normal pressure, but can also be carried out under increased or reduced pressure.
  • the desired compounds of the formula (I) can be isolated, for example, by subsequent filtration or extraction. Such methods are known to the person skilled in the art.
  • reaction vessel were 648.8 g of toluene, 153.9 g [1.09 mol] 1,1,1-trifluoro-2-isothiocyanatoethane, 170.3 g [1.23 mol] potassium carbonate and 165.9 g [1.09 mol] methyl bromoacetate submitted.
  • the reaction mixture was heated to 50 ° C. with stirring. At this temperature, a solution of 235.8 g [0.986 mol] of 2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] aniline in 235.8 g of toluene was added dropwise over the course of 30 minutes, with continued stirring .
  • reaction mixture was then stirred at 50 ° C. for 7 hours, cooled to 20 ° C. over the course of 2 hours and stirred at 20 ° C. for a further 12 hours.
  • the reaction mixture was a readily stirrable suspension all the time.
  • the reaction mixture was metered into 672.8 g of water with stirring.
  • the reaction vessel was rinsed with 259.5 g of toluene and the rinsing solution was also metered into the water.
  • the upper, organic phase was separated off and stirred with 270 g of hydrochloric acid (16%).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un procédé de fabrication de 2-(phénylimino)-1,3-thiazolidine-4-ones de formule générale (I) dans laquelle Y1, Y2, R1, R2 et R3 ont les significations indiquées dans la description.
EP20735624.7A 2019-07-10 2020-07-08 Procédé de fabrication de 2-(phénylimino)-1,3-thiazolidine-4-ones Pending EP3997075A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP19185383 2019-07-10
PCT/EP2020/069171 WO2021005081A1 (fr) 2019-07-10 2020-07-08 Procédé de fabrication de 2-(phénylimino)-1,3-thiazolidine-4-ones

Publications (1)

Publication Number Publication Date
EP3997075A1 true EP3997075A1 (fr) 2022-05-18

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP20735624.7A Pending EP3997075A1 (fr) 2019-07-10 2020-07-08 Procédé de fabrication de 2-(phénylimino)-1,3-thiazolidine-4-ones

Country Status (10)

Country Link
US (1) US20220315545A1 (fr)
EP (1) EP3997075A1 (fr)
JP (1) JP2022540114A (fr)
KR (1) KR20220034818A (fr)
CN (1) CN114040910A (fr)
BR (1) BR112022000185A2 (fr)
IL (1) IL289651A (fr)
MX (1) MX2022000421A (fr)
TW (1) TW202116743A (fr)
WO (1) WO2021005081A1 (fr)

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EP0985670A1 (fr) * 1998-08-13 2000-03-15 American Cyanamid Company Composés de 1-(3-hétérocyclylphényl)isothiourée, -isourée, -guanidine et -amidine comme herbicides
FR2796643B1 (fr) * 1999-07-22 2005-04-29 Sod Conseils Rech Applic Derives de 2-arylimino-2, 3-dihydrothiazoles, leurs procedes de preparation et leur utilisation therapeutique
US7365205B2 (en) 2001-06-20 2008-04-29 Daiichi Sankyo Company, Limited Diamine derivatives
DE10250743A1 (de) 2002-10-31 2004-05-19 Boehringer Ingelheim Pharma Gmbh & Co. Kg Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel
ES2523401T3 (es) * 2006-11-23 2014-11-25 Actelion Pharmaceuticals Ltd. Intermedios de un nuevo procedimiento para la preparación de derivados de 5-benciliden-2-alquilimino-3- feniltiazolidin-4-ona
CN103690542B (zh) * 2006-12-28 2015-11-18 Abbvie公司 聚(adp-核糖)聚合酶抑制剂
JP5280972B2 (ja) 2009-08-20 2013-09-04 日本曹達株式会社 殺ダニ剤および新規ウレア化合物
CN102367240B (zh) * 2011-01-25 2014-06-18 华东理工大学 含1,2,3-噻二唑母环的酰亚胺基噻唑酮化合物、中间体及其应用
EP2606726A1 (fr) * 2011-12-21 2013-06-26 Bayer CropScience AG Dérivés de trifluoroéthylsulfure substitués par du N-arylamidine en tant qu'acaricides et insecticides
TWI652012B (zh) 2013-05-20 2019-03-01 杜邦股份有限公司 殺真菌吡唑的固態形式
WO2014202510A1 (fr) 2013-06-20 2014-12-24 Bayer Cropscience Ag Dérivés d'arylsulfure et d'arylsulfoxyde utilisés comme acaricides et insecticides
BR112016023017B1 (pt) 2014-04-04 2021-06-15 Bayer Cropscience Aktiengesellschaft Uso de derivados de sulfóxido de trifluoroetila substituídos por n-arilamidina para o controle de pragas de ácaros
WO2018127292A1 (fr) * 2017-01-06 2018-07-12 Universität Bern Inhibiteurs sélectifs de la kinase aurora a
CN107935961B (zh) * 2017-12-01 2019-10-29 赣南师范大学 一种2-亚氨基噻唑烷-4-酮类化合物的制备方法

Also Published As

Publication number Publication date
TW202116743A (zh) 2021-05-01
BR112022000185A2 (pt) 2022-02-22
JP2022540114A (ja) 2022-09-14
IL289651A (en) 2022-03-01
WO2021005081A1 (fr) 2021-01-14
CN114040910A (zh) 2022-02-11
MX2022000421A (es) 2022-02-10
KR20220034818A (ko) 2022-03-18
US20220315545A1 (en) 2022-10-06

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