JPS5492961A - Production of 5-arylhydantoin - Google Patents

Production of 5-arylhydantoin

Info

Publication number
JPS5492961A
JPS5492961A JP15778377A JP15778377A JPS5492961A JP S5492961 A JPS5492961 A JP S5492961A JP 15778377 A JP15778377 A JP 15778377A JP 15778377 A JP15778377 A JP 15778377A JP S5492961 A JPS5492961 A JP S5492961A
Authority
JP
Japan
Prior art keywords
acid
formula
aryl
reaction
medium
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.)
Granted
Application number
JP15778377A
Other languages
Japanese (ja)
Other versions
JPS5757033B2 (en
Inventor
Arahiko Eguchi
Fusayoshi Kakizaki
Toshio Iwagami
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.)
Ajinomoto Co Inc
Original Assignee
Ajinomoto Co Inc
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 Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Priority to JP15778377A priority Critical patent/JPS5492961A/en
Priority to GB7850228A priority patent/GB2012756B/en
Publication of JPS5492961A publication Critical patent/JPS5492961A/en
Publication of JPS5757033B2 publication Critical patent/JPS5757033B2/ja
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C07D233/78—Radicals substituted by oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

PURPOSE: Title compound useful as an intermediate of α-aryl-α-aminoacetic acid (a modifier of semisynthetic penicillin) is efficiently produced from safe and industrially available α-aryl-α-hydroxyacetic acid or its precursor and urea.
CONSTITUTION: The reaction of α-aryl-α-hydroxyacetic acid as p-hydroxymandelic acid of formula I (R1 is p- or o-substituted OH, 1W6C alkoxy or alkyl, halogen, acylated amino, NO2) with urea in an amount of preferably 2W10 times the molar quantity of the hydroxyacetic acid is conducted in an acidic medium, preferably aqueous sulfuric or hydrochloric acid medium, much preferably 5W25% concentration of sulfuric or hydrochloric acid to produce 5-arylhydantoin of formula II. The compound of formula I is prepared by reaction of glyoxylic acid with a compound of formula III in an alkaline aqueous medium and the product can be used for the subsequent reaction without the isolation of the comound of formula I.
COPYRIGHT: (C)1979,JPO&Japio
JP15778377A 1977-12-29 1977-12-29 Production of 5-arylhydantoin Granted JPS5492961A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP15778377A JPS5492961A (en) 1977-12-29 1977-12-29 Production of 5-arylhydantoin
GB7850228A GB2012756B (en) 1977-12-29 1978-12-29 Process for preparing 5-arylhydantoins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP15778377A JPS5492961A (en) 1977-12-29 1977-12-29 Production of 5-arylhydantoin

Publications (2)

Publication Number Publication Date
JPS5492961A true JPS5492961A (en) 1979-07-23
JPS5757033B2 JPS5757033B2 (en) 1982-12-02

Family

ID=15657192

Family Applications (1)

Application Number Title Priority Date Filing Date
JP15778377A Granted JPS5492961A (en) 1977-12-29 1977-12-29 Production of 5-arylhydantoin

Country Status (2)

Country Link
JP (1) JPS5492961A (en)
GB (1) GB2012756B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4457939A (en) * 1982-11-01 1984-07-03 Pfizer Inc. Aldose reductase inhibiting 5-(2-alkoxy-3-substituted phenyl)hydantoins
EP0112620B1 (en) * 1982-11-01 1986-12-30 Pfizer Inc. 5-(substituted phenyl) hydantoins
ES2018743A6 (en) * 1989-11-29 1991-05-01 Etilo Derivados Preparing 5-(4-hydroxyphenyl)hydantoin
JP2974742B2 (en) * 1990-09-04 1999-11-10 鐘淵化学工業株式会社 Method for producing 5-arylhydantoins
AT398199B (en) * 1992-11-27 1994-10-25 Chemie Linz Gmbh METHOD FOR PRODUCING ARYLHYDANTOINES
EP0989122B1 (en) 1998-09-22 2003-05-21 Degussa AG Process for the preparation of imidazolidine-2,4-diones

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53116373A (en) * 1977-03-18 1978-10-11 Kanegafuchi Chem Ind Co Ltd Preparation of 5-(4-hydroxyphenyl)hydantoin

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53116373A (en) * 1977-03-18 1978-10-11 Kanegafuchi Chem Ind Co Ltd Preparation of 5-(4-hydroxyphenyl)hydantoin

Also Published As

Publication number Publication date
GB2012756A (en) 1979-08-01
GB2012756B (en) 1982-06-30
JPS5757033B2 (en) 1982-12-02

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