WO1993022300A1 - Procede de production de 2-phenyl-benzoxazin-4-one - Google Patents

Procede de production de 2-phenyl-benzoxazin-4-one Download PDF

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Publication number
WO1993022300A1
WO1993022300A1 PCT/GB1993/000822 GB9300822W WO9322300A1 WO 1993022300 A1 WO1993022300 A1 WO 1993022300A1 GB 9300822 W GB9300822 W GB 9300822W WO 9322300 A1 WO9322300 A1 WO 9322300A1
Authority
WO
WIPO (PCT)
Prior art keywords
anhydride
process according
reaction
isatoic anhydride
benzoic
Prior art date
Application number
PCT/GB1993/000822
Other languages
English (en)
Inventor
Michael Lancaster
Original Assignee
Bp Chemicals Limited
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
Priority claimed from GB929208792A external-priority patent/GB9208792D0/en
Priority claimed from GB929209038A external-priority patent/GB9209038D0/en
Application filed by Bp Chemicals Limited filed Critical Bp Chemicals Limited
Publication of WO1993022300A1 publication Critical patent/WO1993022300A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
    • C07D265/22—Oxygen atoms

Definitions

  • the present invention relates to a process for the production of compounds of the 2-phenyl-4H-3,l-benozoxazin-4-one (hereafter "2PB4") type directly from the corresponding isatoic anhydride without having to resort to the use of acid halides or nitrogenous bases.
  • 2PB4 2-phenyl-4H-3,l-benozoxazin-4-one
  • the present invention is a process for the production of compounds of the 2PB4 type, said process comprising reacting the corresponding isatoic anhydride with benzoic anhydride at elevated temperature in the absence of a base, optionally in the presence of a solvent.
  • Isatoic anhydride is a well established chemical and can be obtained commercially in high grades of purity.
  • 2PB4 type is meant here and throughout the specification the basic 2PB4 structure as defined herein above and any nuclear substituents groups carried by the basic structure which do not interfere with the reaction of producing a benzoxazinone structure from benzoic anhydride and the corresponding isatoic anhydride.
  • substituent groups may be one or more of alkyl, aryl, alkaryl, aralkyl groups or halogen atoms. It will be understood by those skilled in the art that in order to produce a 2PB4 type structure which carries such substituents, the starting isatoic anhydride must also carry the corresponding substituents in its nucleus.
  • a solvent when used, is suitably a ketone such as methyl ethyl ketone, a carboxylic acid such as acetic acid, a nitrile such as a benzonitrile, an ester such as methyl benzoate or a diglyme and is preferably diglyme.
  • the mol ratio of isatoic anhydride to benzoic anhydride in the latter reaction is suitably in the range from 1:1 to 1:3, preferably in the range from 1:1 to 1:1.5. Substantially equimolar amounts of the reactants is most preferred.
  • the reactants are suitably mixed with the solvent and refluxed for a duration at a temperature in the range from 100°C to 250°C, preferably in the range from 120° to 200°C.
  • the main by-product of this reaction is benzoic acid which can be separated from the desired 2PB4 type product by conventional techniques, eg distillation.
  • 2PB4 type products are very desirable because they can be used as a bleach activator in detergent formulations as claimed and described in our published EP-A-332294. They enhance the low temperature bleaching activity of conventional bleaches.
  • the process of the present invention is further illustrated with reference to the following Examples: Example 1 (Isatoic Anhydride + Benzoic Anhydride in Diglyme) :

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne un procédé pour la préparation de composés du type 2-phényl-benzoxazin-4-one (2PB4) en faisant réagir l'anhydride isatoïque correspondant avec de l'anhydride benzoïque à température élevée, le cas échéant en présence d'un solvant. Le procédé offre l'avantage que la réaction s'effectue sans avoir à recourir à des halogénures d'acides ou à des bases azotées. Les produits du type 2PB4 sont utiles comme activateurs d'agents de blanchiment.
PCT/GB1993/000822 1992-04-23 1993-04-20 Procede de production de 2-phenyl-benzoxazin-4-one WO1993022300A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB929208792A GB9208792D0 (en) 1992-04-23 1992-04-23 Organic synthesis
GB9208792.3 1992-04-23
GB9209038.0 1992-04-25
GB929209038A GB9209038D0 (en) 1992-04-25 1992-04-25 Organic synthesis

Publications (1)

Publication Number Publication Date
WO1993022300A1 true WO1993022300A1 (fr) 1993-11-11

Family

ID=26300765

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1993/000822 WO1993022300A1 (fr) 1992-04-23 1993-04-20 Procede de production de 2-phenyl-benzoxazin-4-one

Country Status (1)

Country Link
WO (1) WO1993022300A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003035735A1 (fr) * 2001-10-22 2003-05-01 Cytec Technology Corp. Absorbeurs uv a base de benzoxazinone a faible teneur en sodium et a faible indice de coloration et procede de fabrication de ces absorbeurs
EP1806345A1 (fr) * 2006-01-05 2007-07-11 TEMSA International Inc. Procédé pour la préparation d'un benzoxazinone

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2241012A1 (de) * 1971-08-30 1973-03-15 Chinoin Gyogyszer Es Vegyeszet Neue 3,1-benzoxazin-4-on-derivate und verfahren zur herstellung derselben
FR2301524A1 (fr) * 1975-02-20 1976-09-17 Sherwin Williams Co Procede de preparation de benzoxazines
EP0017931A2 (fr) * 1979-04-12 1980-10-29 BASF Aktiengesellschaft Dérivés de 4H-3,1-benzoxazine, procédés pour leur préparation et leur utilisation dans la lutte contre la végétation indésirable
EP0032242A1 (fr) * 1980-01-05 1981-07-22 BASF Aktiengesellschaft Dérivés de 4H-3,1-benzoxazine, procédé pour leur préparation et leur application dans la lutte contre la croissance des plantes indésirables
EP0049398A1 (fr) * 1980-10-08 1982-04-14 BASF Aktiengesellschaft Dérivés de 4H-3,1-benzoxazines, procédé pour leur préparation et leur utilisation comme herbicide
EP0199276A2 (fr) * 1985-04-19 1986-10-29 BASF Aktiengesellschaft Procédé de préparation de 2-phényl-4H-3,1-benzoxazines substituées
WO1992012971A1 (fr) * 1991-01-18 1992-08-06 Basf Aktiengesellschaft Procede de production de 4h-3,1-benzoxazin-4-ones

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2241012A1 (de) * 1971-08-30 1973-03-15 Chinoin Gyogyszer Es Vegyeszet Neue 3,1-benzoxazin-4-on-derivate und verfahren zur herstellung derselben
FR2301524A1 (fr) * 1975-02-20 1976-09-17 Sherwin Williams Co Procede de preparation de benzoxazines
EP0017931A2 (fr) * 1979-04-12 1980-10-29 BASF Aktiengesellschaft Dérivés de 4H-3,1-benzoxazine, procédés pour leur préparation et leur utilisation dans la lutte contre la végétation indésirable
EP0032242A1 (fr) * 1980-01-05 1981-07-22 BASF Aktiengesellschaft Dérivés de 4H-3,1-benzoxazine, procédé pour leur préparation et leur application dans la lutte contre la croissance des plantes indésirables
EP0049398A1 (fr) * 1980-10-08 1982-04-14 BASF Aktiengesellschaft Dérivés de 4H-3,1-benzoxazines, procédé pour leur préparation et leur utilisation comme herbicide
EP0199276A2 (fr) * 1985-04-19 1986-10-29 BASF Aktiengesellschaft Procédé de préparation de 2-phényl-4H-3,1-benzoxazines substituées
WO1992012971A1 (fr) * 1991-01-18 1992-08-06 Basf Aktiengesellschaft Procede de production de 4h-3,1-benzoxazin-4-ones

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003035735A1 (fr) * 2001-10-22 2003-05-01 Cytec Technology Corp. Absorbeurs uv a base de benzoxazinone a faible teneur en sodium et a faible indice de coloration et procede de fabrication de ces absorbeurs
US6774232B2 (en) 2001-10-22 2004-08-10 Cytec Technology Corp. Low color, low sodium benzoxazinone UV absorbers and process for making same
EP1806345A1 (fr) * 2006-01-05 2007-07-11 TEMSA International Inc. Procédé pour la préparation d'un benzoxazinone
WO2007077228A1 (fr) * 2006-01-05 2007-07-12 Temsa International Inc. Procede de fabrication d’une benzoxazinone
US7915406B2 (en) 2006-01-05 2011-03-29 Temsa International Inc. Process for preparing a benzoxazinone

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