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GB716137A - Preparation of methionine hydantoin - Google Patents

Preparation of methionine hydantoin

Info

Publication number
GB716137A
GB716137A GB30017/51A GB3001751A GB716137A GB 716137 A GB716137 A GB 716137A GB 30017/51 A GB30017/51 A GB 30017/51A GB 3001751 A GB3001751 A GB 3001751A GB 716137 A GB716137 A GB 716137A
Authority
GB
United Kingdom
Prior art keywords
cyanide
hydantoin
methionine
ammonium
propaldehyde
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.)
Expired
Application number
GB30017/51A
Inventor
David Oliver Holland
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.)
Beecham Research Laboratories Ltd
Original Assignee
Beecham Research Laboratories Ltd
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 Beecham Research Laboratories Ltd filed Critical Beecham Research Laboratories Ltd
Priority to GB30017/51A priority Critical patent/GB716137A/en
Publication of GB716137A publication Critical patent/GB716137A/en
Expired 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
    • 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
    • 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
    • C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Methionine hydantoin is prepared by reacting b -methyl thio propaldehyde with ammonium carbonate, ammonium bicarbonate, ammonium carbamate or ammonia and carbon dioxide, and an inorganic cyanide in the presence of a tertiary alkylamine. The amine is preferably present in amounts of at least one mol. per mol. of aldehyde. The reaction may be effected at room or elevated temperature and may be operated continuously. The inorganic cyanide may be an alkali metal or earth metal cyanide or hydrogen cyanide. The hydantoin may be hydrolysed to methionine. In an example, b -methylthio propaldehyde is added to a solution of sodium cyanide, ammonium carbonate and triethylamine in aqueous alcohol and the desired hydantoin is isolated from the resulting product. Reference is also made to the use of tri-methylamine and tri-n-butylamine. Specification 630,139 is referred to. According to the Provisional Specification, any tertiary amine having a stronger basicity than ammonia may be used.
GB30017/51A 1951-12-21 1951-12-21 Preparation of methionine hydantoin Expired GB716137A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB30017/51A GB716137A (en) 1951-12-21 1951-12-21 Preparation of methionine hydantoin

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB30017/51A GB716137A (en) 1951-12-21 1951-12-21 Preparation of methionine hydantoin

Publications (1)

Publication Number Publication Date
GB716137A true GB716137A (en) 1954-09-29

Family

ID=10300927

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30017/51A Expired GB716137A (en) 1951-12-21 1951-12-21 Preparation of methionine hydantoin

Country Status (1)

Country Link
GB (1) GB716137A (en)

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