WO1996034861A1 - Nouveau procede de n2-tritylation de cycles tetrazole - Google Patents

Nouveau procede de n2-tritylation de cycles tetrazole Download PDF

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Publication number
WO1996034861A1
WO1996034861A1 PCT/JP1996/001195 JP9601195W WO9634861A1 WO 1996034861 A1 WO1996034861 A1 WO 1996034861A1 JP 9601195 W JP9601195 W JP 9601195W WO 9634861 A1 WO9634861 A1 WO 9634861A1
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WO
WIPO (PCT)
Prior art keywords
group
optionally substituted
carbon atoms
linear
substituted
Prior art date
Application number
PCT/JP1996/001195
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English (en)
Japanese (ja)
Inventor
Ginro Tokuhara
Tadashi Yamaguchi
Tetsuya Iwasaki
Kazunori Monzen
Original Assignee
Chugoku Kayaku Kabushiki Kaisha
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 Chugoku Kayaku Kabushiki Kaisha filed Critical Chugoku Kayaku Kabushiki Kaisha
Priority to AU55157/96A priority Critical patent/AU5515796A/en
Publication of WO1996034861A1 publication Critical patent/WO1996034861A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings

Definitions

  • the present invention relates to a novel process for producing 5-substituted 1-2-trityl-2H-tetrazole from a 5-substituted tetrazole and trityl alcohol by using an acid as a catalyst.
  • N2-tritylation when performing tritylation of the 2-position N atom of the tetrazole ring (hereinafter, the tritiation of the 2-position N atom is referred to as “N2-tritylation”), tetrazole compounds are converted to alkali (eg, hydroxylated). N2-tritylation was carried out by the action of triphenylmethyl chloride (also known as trifluoromethane or trityl chloride) in sodium, alkylamine, pyridine, etc.).
  • triphenylmethyl chloride also known as trifluoromethane or trityl chloride
  • triphenylmethyl chloride is expensive and has a problem that it is difficult to handle because it is sensitive to moisture (decomposes and dissolves in water). Disclosure of the invention
  • the present invention provides a method for N 2 -tritylation of a tetrazole ring using a trityling agent which is easy to handle and inexpensive.
  • the present invention provides a compound represented by the formula (I):
  • R represents an optional substituent
  • the kind of the acid used as a catalyst in the present invention may be an inorganic acid or an organic acid, and is not particularly limited.
  • Preferred acids include sulfuric acid (particularly concentrated sulfuric acid), hydrochloric acid, phosphoric acid and the like.
  • Trityl alcohol used in the present invention is easier to handle (higher stability against water) than triphenylmethyl chloride, and the unit cost is about half, so that the production cost can be reduced. It is industrially very suitable.
  • the substituent R at the 5-position of the tetrazole represented by the formula (I) may be any substituent and is not particularly limited.
  • R is hydrogen, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted, an alkylthio group which may be substituted.
  • Optionally substituted alkoxy group optionally substituted alkylthio group, optionally substituted alkylsulfinyl group, optionally substituted alkylsulfonyl group, optionally substituted alkylamino group, fully substituted Alkenyloxy group, alkenylthio group which may be substituted, alkoxycarbonyl group which may be substituted, aryl group which may be substituted, aryloxy group which may be substituted, Selected from the group consisting of an optionally substituted aralkyl group, an optionally substituted arylarylalkenyl group, and an optionally substituted heterocyclic group.
  • substituents which may be substituted in each of these groups include, for example, halogen (fluoro, chloro, bromo, and sulfide), linear or branched having 1 to 4 carbon atoms.
  • An alkyl group e.g., a methyl group, an ethyl group, etc.
  • a linear or branched alkoxy group having 1 to 4 carbon atoms e.g., a methoxy group, an ethoxy group, etc.
  • a chain or branched alkylthio group eg, methylthio group, ethylthio group, etc.
  • a linear or branched alkylsulfinyl group having 1 to 4 carbon atoms eg, methanesulfinyl group
  • carbon A linear or branched alkylsulfonyl group e.g., mesyl group of 1 to 4; a nitro group, an amino group, an aldehyde group
  • R is hydrogen, a linear or branched alkyl group which may be substituted and has 1 to 4 carbon atoms (for example, a methyl group, an ethyl group, etc.), and 1 to 4 carbon atoms.
  • a straight-chain or branched-chain optionally substituted alkoxy group for example, a methoxy group or an ethoxyquin group
  • a straight-chain or branched-chain alkylthio group having 1 to 4 carbon atoms for example, A methylthio group, an ethylthio group, etc.
  • a linear or branched alkylsulfinyl group having 1 to 4 carbon atoms for example, methanesulfinyl group
  • halogen fluoro, chloro, bromo, odo
  • a linear or branched alkyl group having 1 to 4 carbon atoms eg, a methyl group, an ethyl group, etc.
  • a carbon number of 1 to 4 A straight-chain or branched alkoxy group (eg, methoxy group, ethoxyquin group, etc.); a straight-chain or branched alkylthio group having 1 to 4 carbon atoms (eg, methylthio group, ethylthio group) Etc.
  • a linear or branched alkylsulfinyl group having 1 to 4 carbon atoms e.g., methanesulfinyl group
  • a linear or branched alkylsulfonyl group having 1 to 4 carbon atoms e.g., A mesyl group
  • halogen Fluoro, black hole, bromo, ® one de
  • linear or branched alkyl group e.g., methyl group having 1 to 4 carbon atoms, Echiru
  • a straight-chain or branched alkoxy group having 1 to 4 carbon atoms for example, methoxy group, ethoxy group, etc.
  • a straight-chain or branched alkylthio group having 1 to 4 carbon atoms.
  • Group eg, methylthio group, ethylthio group, etc.
  • linear or branched alkylsulfinyl group having 1 to 4 carbon atoms eg, methanesulfinyl group
  • linear or branched group having 1 to 4 carbon atoms eg, methanesulfinyl group
  • a disubstituted phenyl group represented by a branched alkylsulfonyl group for example, mesyl group
  • a nitro group an amino group, an aldehyde group, or a carboxyl group
  • a 5-substituted tetrazole compound as a starting material, trityl alcohol and a solvent eg, benzene, toluene, xylene, etc.
  • a solvent eg, benzene, toluene, xylene, etc.
  • an acid eg, (Sulfuric acid)
  • the reaction is carried out while stirring and heating to reflux.
  • an acid eg, (Sulfuric acid)
  • desiccant organic layer existing purpose was dried, the target compound can be obtained and the solvent was distilled off.
  • Example 2 After the completion of the reaction, the same post-treatment as in Example 1 was performed to obtain 0.5 g of white crystals. Melting point: 166.3-177.2 ° C. Yield after recrystallization: 91.9% (based on trityl alcohol).
  • Trityl alcohol used in the method of the present invention is easier to handle and has a unit price of about half that of the conventional trityling agent, trifuunylmethyl chloride, so that the production cost can be reduced. It is industrially very suitable.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention porte sur un procédé de préparation de 2-trityl-2H-tétrazole substitué en 5 de formule générale (II) (dans laquelle R est un substituant arbitraire) à partir d'un tétrazole substitué en 5 de formule générale (I) (dans laquelle R est défini comme ci-dessus) et d'un alcool tritylique à l'aide d'un catalyseur. L'alcool tritylique est plus facile à manipuler que le chlorure de triphénylméthyle utilisé antérieurement comme agent de tritylation et d'un coût deux fois moindre, ce qui présente des avantages sur le plan industriel.
PCT/JP1996/001195 1995-05-02 1996-05-01 Nouveau procede de n2-tritylation de cycles tetrazole WO1996034861A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU55157/96A AU5515796A (en) 1995-05-02 1996-05-01 Novel process for the n2-tritylation of tetrazole ring

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP10861095 1995-05-02
JP7/108610 1995-05-02

Publications (1)

Publication Number Publication Date
WO1996034861A1 true WO1996034861A1 (fr) 1996-11-07

Family

ID=14489171

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1996/001195 WO1996034861A1 (fr) 1995-05-02 1996-05-01 Nouveau procede de n2-tritylation de cycles tetrazole

Country Status (2)

Country Link
AU (1) AU5515796A (fr)
WO (1) WO1996034861A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5673075A (en) * 1979-11-19 1981-06-17 Sumitomo Chem Co Ltd Preparation of n-substituted triazole
JPS58189167A (ja) * 1982-04-30 1983-11-04 Kyowa Hakko Kogyo Co Ltd Ｎ−置換イミダゾ−ル類の製造法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5673075A (en) * 1979-11-19 1981-06-17 Sumitomo Chem Co Ltd Preparation of n-substituted triazole
JPS58189167A (ja) * 1982-04-30 1983-11-04 Kyowa Hakko Kogyo Co Ltd Ｎ−置換イミダゾ−ル類の製造法

Also Published As

Publication number Publication date
AU5515796A (en) 1996-11-21

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