GB716136A - Preparation of methionine hydantoin - Google Patents

Preparation of methionine hydantoin

Info

Publication number
GB716136A
GB716136A GB30016/51A GB3001651A GB716136A GB 716136 A GB716136 A GB 716136A GB 30016/51 A GB30016/51 A GB 30016/51A GB 3001651 A GB3001651 A GB 3001651A GB 716136 A GB716136 A GB 716136A
Authority
GB
United Kingdom
Prior art keywords
methionine
nitrile
hydantoin
amine
carbon dioxide
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
GB30016/51A
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 GB30016/51A priority Critical patent/GB716136A/en
Publication of GB716136A publication Critical patent/GB716136A/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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (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 methionine nitrile with carbon dioxide in the presence of an aliphatic amine containing not more than twelve carbon atoms. The amines may be primary, secondary or tertiary and are preferably alkylamines, alkanolamines or alkyl alkanol amines; they are preferably used in amounts of at least one mol. per mol. of nitrile. The hydantoin may be hydrolysed to methionine by alkaline hydrolysing agents without being isolated. In an example, carbon dioxide is bubbled through an aqueous alcoholic solution of the nitrile containing triethylamine, yielding 90 per cent of the hydantoin; trimethylamine, b -diethylaminoethanol, diethylamine, tri-n-butylamine, triethanolamine, diethanolamine and isopropylamine may be used similarly. According to the Provisional Specification, the amine may be any tertiary amine of a basicity greater than that of methionine nitrile.
GB30016/51A 1951-12-21 1951-12-21 Preparation of methionine hydantoin Expired GB716136A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB30016/51A GB716136A (en) 1951-12-21 1951-12-21 Preparation of methionine hydantoin

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB30016/51A GB716136A (en) 1951-12-21 1951-12-21 Preparation of methionine hydantoin

Publications (1)

Publication Number Publication Date
GB716136A true GB716136A (en) 1954-09-29

Family

ID=10300910

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30016/51A Expired GB716136A (en) 1951-12-21 1951-12-21 Preparation of methionine hydantoin

Country Status (1)

Country Link
GB (1) GB716136A (en)

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