GB806931A - Improvements in or relating to the production of 5-(4-hydroxybutyl) hydantoin and intermediates therefor - Google Patents

Improvements in or relating to the production of 5-(4-hydroxybutyl) hydantoin and intermediates therefor

Info

Publication number
GB806931A
GB806931A GB16288/56A GB1628856A GB806931A GB 806931 A GB806931 A GB 806931A GB 16288/56 A GB16288/56 A GB 16288/56A GB 1628856 A GB1628856 A GB 1628856A GB 806931 A GB806931 A GB 806931A
Authority
GB
United Kingdom
Prior art keywords
ammonia
hydantoin
product
acid
aqueous
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
GB16288/56A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB806931A publication Critical patent/GB806931A/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
    • C07D233/78—Radicals substituted by oxygen atoms

Landscapes

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

Abstract

The invention comprises (1) an aqueous solution of a -amino-e -hydroxy-capronitrile, and its preparation by reacting g -hydroxyvaleraldehyde, hydrogen cyanide and ammonia in aqueous medium without allowing the aldehyde and HCN to come into contact in a non-acid medium unless the ammonia is present; and (2) the preparation of 5-(4-hydroxy-butyl)-hydantoin from the said capronitrile by reaction with carbon dioxide. The first step may be carried out by adding the components simultaneously to an aqueous medium, or by rapidly adding the ammonia to a non-alkaline mixture of the other two reactants, e.g. one of pH 1-6. The quantities are preferably around stoichiometric, e.g. aldehyde / cyanide / ammonia as 1 : 1 : 1.2. The temperature may be 10-40 DEG C., and the ammonia may be aqueous or anhydrous. The hydroxyvaleraldehyde can be used as the acid hydrolysis product of dihydropyran. An example is given of the process, the product being detected by paper chromatography and by acid hydrolysis to a -amino-e -hydroxycaproic acid. The formation of the hydantoin may be carried out by direct carbonation of the reaction product of the first step, preferably at elevated pressure and temperature, e.g. 60-120 DEG C.; this step is also exemplified. The product is an intermediate in the synthesis of lysine.
GB16288/56A 1955-05-25 1956-05-25 Improvements in or relating to the production of 5-(4-hydroxybutyl) hydantoin and intermediates therefor Expired GB806931A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US806931XA 1955-05-25 1955-05-25

Publications (1)

Publication Number Publication Date
GB806931A true GB806931A (en) 1959-01-07

Family

ID=22159009

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16288/56A Expired GB806931A (en) 1955-05-25 1956-05-25 Improvements in or relating to the production of 5-(4-hydroxybutyl) hydantoin and intermediates therefor

Country Status (1)

Country Link
GB (1) GB806931A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT382366B (en) * 1985-03-15 1987-02-25 Lim Kunststoff Tech Gmbh Process for the preparation of novel alpha-amino- hydroxyalkyl nitriles
US6284901B1 (en) 1999-12-17 2001-09-04 Dixie Chemical Company Dinitrile intermediates for the synthesis of omapatrilat and methods for producing same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT382366B (en) * 1985-03-15 1987-02-25 Lim Kunststoff Tech Gmbh Process for the preparation of novel alpha-amino- hydroxyalkyl nitriles
US6284901B1 (en) 1999-12-17 2001-09-04 Dixie Chemical Company Dinitrile intermediates for the synthesis of omapatrilat and methods for producing same

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