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WO2001049660A1 - Processus de preparation de 3-{[3-chloro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedione - Google Patents

Processus de preparation de 3-{[3-chloro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedione Download PDF

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Publication number
WO2001049660A1
WO2001049660A1 PCT/FI2000/001150 FI0001150W WO0149660A1 WO 2001049660 A1 WO2001049660 A1 WO 2001049660A1 FI 0001150 W FI0001150 W FI 0001150W WO 0149660 A1 WO0149660 A1 WO 0149660A1
Authority
WO
WIPO (PCT)
Prior art keywords
chloro
pentanedione
methylsulfonyl
propanol
amine
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.)
Ceased
Application number
PCT/FI2000/001150
Other languages
English (en)
Inventor
Kari Lönnberg
Reijo Bäckström
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.)
Orion Oyj
Original Assignee
Orion Oyj
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 Orion Oyj filed Critical Orion Oyj
Priority to AU25196/01A priority Critical patent/AU2519601A/en
Priority to GB0215787A priority patent/GB2373249B/en
Publication of WO2001049660A1 publication Critical patent/WO2001049660A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system

Definitions

  • the present invention relates to a process for preparing a new molecule, 3- ⁇ [3-chloro- 4-(methylsulfonyl)phenyl]methylene ⁇ -2,4-pentanedione, having a structure (I)
  • Patent application EP 0 440 324 describes substituted diketones and their use.
  • the preparation of several molecules with analogous structures to (I) has been described.
  • Eg. toluene, tetrahydrofurane, trifluoroacetic acid and 2-propanol have been mentioned as suitable solvents in the processes.
  • piperidine and acetic acid or thionyl chloride as catalysts.
  • Eg. 3-[(4- methylsulfonylphenyl)methylene]-2,4-pentanedione has been prepared in 2-propanol using thionyl chloride as a catalyst. The solution is evaporated to dryness in vacuo and the product is crystallized from toluene.
  • 3- [(3, 4- dichlorophenyl)methylene]-2,4-pentanedione is prepared using toluene as a solvent and piperidine and acetic acid as catalyst. Anyhow, none of the examples describe 3- ⁇ [3-chloro-4-(methylsulfonyl)phenyl]methylene ⁇ -2,4-pentanedione, nor the use of 2- propanol as a solvent with an amine as a catalyst in the preparation of similar compounds.
  • the object of this invention is the preparation of 3- ⁇ [3-chloro-4- (methylsulfonyl)phenyl]methylene ⁇ -2,4-pentanedione from 3-chloro-4- (methylsulfonyl)benzaldehyde (II)
  • 3-Chloro-4-(methylsulfonyl)benzaldehyde (II) can be prepared eg. from halogenated benzaldehydes, eg. 3-chloro-4-fluorobenzaldehyde or 3,4-dichlorobenzaldehyde and sodium salt of methanesulfinic acid, eg. from 3,4-dichlorobenzaldehyde and methanesulfinic sodium salt as described in example 1.
  • compound (I) is prepared by the process according to the invention, compound (II) is allowed to react with compound (III) in 2-propanol or in the mixture of 2- propanol and DMF in the presence of an amine, preferably a secondary amine and most preferably piperidine or in the presence of amine and a weak acid, preferably organic acid and most preferably acetic acid or formic acid.
  • the acid is used in proportion to amine from 0 to 4 equivalence, preferably in proportion 1 : 1.
  • 2,4- Pentanedione (compound III) is used from 1 to 5 equivalents to 3-chloro-4- (methylsulfonyl)benzaldehyde (compound II), preferably 2 to 3 equivalents.
  • 2-propanol is used 2,5 - 4,5 times the amount of DMF, preferably the ratio of DMF to 2-propanol is from 1:3 to 1 :4, most preferably 1 :3,5.
  • 3,4-Pentanedione is added to a mixture containing 3-chloro-4-(methylsulfonyl)- benzaldehyde, amine and optionally an acid in 2-propanol or in 2-propanol and DMF.
  • the mixture is stirred in ambient temperature overnight.
  • the product is separated by filtration and washed with cold 2-propanol.
  • reaction it is also possible to perform the reaction in higher temperature, about 50 - 70 °C , and use a shorter reaction time, from 1 to 10 hours. After the reaction is complete, the mixture is cooled to and the product is filtered and washed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pulmonology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

On prépare 3-{[3-Chloro-4-(méthylsulfonyl)phényl]méthylène}-2,4-pentanedione à partir de 3-chloro-4-(méthylsulfonyl)benzaldéhyde et 2,4-pentanedione en utilisant 2-propanol ou 2-propanol et un diméthylformamide comme solvant and un amine éventuellement avec un acide faible comme catalyseur.
PCT/FI2000/001150 1999-12-30 2000-12-28 Processus de preparation de 3-{[3-chloro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedione Ceased WO2001049660A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU25196/01A AU2519601A (en) 1999-12-30 2000-12-28 A process for preparing 3-((3-chloro-4-(methylsulfonyl)-phenyl)methylene)-2,4- pentanedione
GB0215787A GB2373249B (en) 1999-12-30 2000-12-28 A process for preparing 3-{[3-chloro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedione

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI19992819 1999-12-30
FI992819 1999-12-30

Publications (1)

Publication Number Publication Date
WO2001049660A1 true WO2001049660A1 (fr) 2001-07-12

Family

ID=8555836

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FI2000/001150 Ceased WO2001049660A1 (fr) 1999-12-30 2000-12-28 Processus de preparation de 3-{[3-chloro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedione

Country Status (3)

Country Link
AU (1) AU2519601A (fr)
GB (1) GB2373249B (fr)
WO (1) WO2001049660A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103613488A (zh) * 2013-11-25 2014-03-05 格林生物科技股份有限公司 一种2-甲基-2-戊烯醛的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0357403A2 (fr) * 1988-09-01 1990-03-07 Orion-Yhtymà„ Oy Bêta-dicétones substituées
EP0440324A2 (fr) * 1990-02-02 1991-08-07 Orion-Yhtymà„ Oy Béta-dicétones disubstitués et leur utilisation
WO2000001667A1 (fr) * 1998-07-01 2000-01-13 Orion Corporation β-DICETONES SUBSTITUEES ET LEURS UTILISATIONS

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0357403A2 (fr) * 1988-09-01 1990-03-07 Orion-Yhtymà„ Oy Bêta-dicétones substituées
EP0440324A2 (fr) * 1990-02-02 1991-08-07 Orion-Yhtymà„ Oy Béta-dicétones disubstitués et leur utilisation
WO2000001667A1 (fr) * 1998-07-01 2000-01-13 Orion Corporation β-DICETONES SUBSTITUEES ET LEURS UTILISATIONS

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103613488A (zh) * 2013-11-25 2014-03-05 格林生物科技股份有限公司 一种2-甲基-2-戊烯醛的制备方法
CN103613488B (zh) * 2013-11-25 2015-09-23 格林生物科技股份有限公司 一种2-甲基-2-戊烯醛的制备方法

Also Published As

Publication number Publication date
GB2373249B (en) 2004-04-14
GB0215787D0 (en) 2002-08-14
AU2519601A (en) 2001-07-16
GB2373249A (en) 2002-09-18

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