WO2017131213A1 - Procédé de production de dérivé de 1h-tétrazole - Google Patents

Procédé de production de dérivé de 1h-tétrazole Download PDF

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Publication number
WO2017131213A1
WO2017131213A1 PCT/JP2017/003066 JP2017003066W WO2017131213A1 WO 2017131213 A1 WO2017131213 A1 WO 2017131213A1 JP 2017003066 W JP2017003066 W JP 2017003066W WO 2017131213 A1 WO2017131213 A1 WO 2017131213A1
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WO
WIPO (PCT)
Prior art keywords
group
formula
groups
azide
reaction
Prior art date
Application number
PCT/JP2017/003066
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English (en)
Japanese (ja)
Inventor
大輔 市成
今川　務
廣川　賢一
史孝 増井
Original Assignee
日本曹達株式会社
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.)
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Publication date
Application filed by 日本曹達株式会社 filed Critical 日本曹達株式会社
Priority to CN201780007186.5A priority Critical patent/CN108473446A/zh
Publication of WO2017131213A1 publication Critical patent/WO2017131213A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • 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

  • a silylalkyl group having a substituent is a group in which at least one hydrogen atom of an alkyl group is substituted with a silyl group having a substituent.
  • the alkyl group substituted with the silyl group may be a linear alkyl group, a branched alkyl group, or a cyclic alkyl group.
  • the alkyl group is preferably a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, or a cyclic alkyl group having 3 to 8 carbon atoms, and has 1 to 8 carbon atoms.
  • the linear alkyl group is more preferable.
  • Z 1 is preferably —CO— or —SO 2 — rather than —CR a1 R b1 —.
  • R 12 is preferably an aryl group having 6 to 10 carbon atoms, more preferably a phenyl group, and specifically, a group represented by the following general formula (s11) is particularly preferable.
  • the flow reactor used in the production method of the present invention includes a raw material inlet, a product outlet, and a flow path that connects these.
  • the raw material is supplied from the raw material introduction port, and the product obtained by the reaction in the flow path is taken out from the product discharge port.
  • the flow path may include an introduction path, and at least one of a mixer section and a reactor section (retention section) as necessary.
  • the introduction path the part of the flow path that connects the raw material inlet and the mixer part
  • the introduction path when there is no mixer part, the flow part that connects the raw material inlet and the reactor part is introduced. It is called a road.
  • the raw material inlet is usually connected to a container filled with the raw material. You may connect the container for storing a product to a product discharge port as needed.
  • the reaction temperature of the reaction solution in the flow reactor is not particularly limited as long as it can sufficiently suppress the risk of decomposition of the azide compound and the product.
  • it is preferably performed in the range of 150 to 250 ° C, more preferably in the range of 150 to 220 ° C.
  • Example 7 [Method of preparing methyl azide] Sodium azide and dimethyl sulfate were reacted in the following flow reactor to synthesize methyl azide.

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

Abstract

La présente invention concerne un procédé de production, à un rendement élevé, d'un dérivé de 1H-tétrazole au moyen d'un réacteur à circulation et au moyen d'un composé azide et d'un composé cyanure en tant que matériaux de départ. Le procédé de production d'un dérivé de 1H-tétrazole de la présente invention comprend la réaction, dans un réacteur à circulation, d'un composé azide représenté par la formule générale (2) (dans la formule, Y1 représente un groupe alkyle ou similaire) avec un composé cyanure représenté par la formule (3) (dans la formule, Z représente -CO- ou similaire, et R12 représente un groupe aryle facultativement substitué), pour obtenir le dérivé de 1H-tétrazole représenté par la formule (1). 0,8 à 1,2 équivalent en moles du composé cyanure représenté par la formule (3) est utilisé par rapport au composé azide représenté par la formule (2), et la concentration initiale dans la solution de réaction du composé azide représenté par la formule (2) est d'au moins 5 % en masse.
PCT/JP2017/003066 2016-01-29 2017-01-27 Procédé de production de dérivé de 1h-tétrazole WO2017131213A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201780007186.5A CN108473446A (zh) 2016-01-29 2017-01-27 1h-四唑衍生物的制造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016-016727 2016-01-29
JP2016016727 2016-01-29

Publications (1)

Publication Number Publication Date
WO2017131213A1 true WO2017131213A1 (fr) 2017-08-03

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Application Number Title Priority Date Filing Date
PCT/JP2017/003066 WO2017131213A1 (fr) 2016-01-29 2017-01-27 Procédé de production de dérivé de 1h-tétrazole

Country Status (2)

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CN (1) CN108473446A (fr)
WO (1) WO2017131213A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013187325A1 (fr) * 2012-06-12 2013-12-19 日本曹達株式会社 Procédé de fabrication d'un composé azide et procédé de fabrication de dérivé de 1h-tétrazole
WO2013187327A1 (fr) * 2012-06-12 2013-12-19 日本曹達株式会社 Procédé de fabrication d'un dérivé de 1h-tétrazole

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013187325A1 (fr) * 2012-06-12 2013-12-19 日本曹達株式会社 Procédé de fabrication d'un composé azide et procédé de fabrication de dérivé de 1h-tétrazole
WO2013187327A1 (fr) * 2012-06-12 2013-12-19 日本曹達株式会社 Procédé de fabrication d'un dérivé de 1h-tétrazole

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
GUTMANN, B. ET AL.: "Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles and Hydrazoic Acid by Using a Safe and Scalable High-Temperature Microreactor Approach", ANGEW. CHEM. INT. ED., vol. 49, no. 39, 2010, pages 7101 - 7105, XP055176764 *
PALDE, P. B. ET AL.: "Safe and Efficient Tetrazole Synthesis in a Continuous-Flow Microreactor", ANGEW. CHEM. INT. ED., vol. 50, no. 15, 2011, pages 3525 - 3528, XP055009296 *
SHIN'ICHIRO FUSE: "Organic Synthesis Using Microflow Reactor", JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY, vol. 70, no. 2, 20 December 0201 (0201-12-20), Japan, pages 177 - 178, XP008175530 *

Also Published As

Publication number Publication date
CN108473446A (zh) 2018-08-31

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