GB758172A - Improvements in or relating to the preparation of amides - Google Patents

Improvements in or relating to the preparation of amides

Info

Publication number
GB758172A
GB758172A GB28493/54A GB2849354A GB758172A GB 758172 A GB758172 A GB 758172A GB 28493/54 A GB28493/54 A GB 28493/54A GB 2849354 A GB2849354 A GB 2849354A GB 758172 A GB758172 A GB 758172A
Authority
GB
United Kingdom
Prior art keywords
citrazinamide
ammonium salt
ammonia
citric acid
alcohol solvent
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
GB28493/54A
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.)
Pfizer Inc
Original Assignee
Pfizer Inc
Charles Pfizer and 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 Pfizer Inc, Charles Pfizer and Co Inc filed Critical Pfizer Inc
Publication of GB758172A publication Critical patent/GB758172A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides

Landscapes

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

Abstract

A process for preparing citrazinamide and the ammonium salt thereof comprises reacting a 1-4 C alkyl ester of citric acid with ammonia at an elevated temperature and under substantially anhydrous conditions in the presence of an alcohol solvent and, if desired, hydrolyzing the ammonium salt thus produced. The mono-, di- and tri-alkyl esters formed by esterifying citric acid with an appropriate alcohol may be employed as starting materials, in particular trimethyl citrate. The reaction is preferably conducted at 125-160 DEG C. and under superatmospheric pressure, using a molar excess of ammonia. The alcohol solvent preferably contains 1-5 carbon atoms, e.g. methanol. The ammonium salt of citrazinamide is hydrolysed to citrazinamide by dissolving in water and acidifying to a pH of 1 to 3.
GB28493/54A 1953-10-08 1954-10-04 Improvements in or relating to the preparation of amides Expired GB758172A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US532339XA 1953-10-08 1953-10-08

Publications (1)

Publication Number Publication Date
GB758172A true GB758172A (en) 1956-10-03

Family

ID=38538943

Family Applications (1)

Application Number Title Priority Date Filing Date
GB28493/54A Expired GB758172A (en) 1953-10-08 1954-10-04 Improvements in or relating to the preparation of amides

Country Status (3)

Country Link
BE (1) BE532339A (en)
DE (1) DE1041963B (en)
GB (1) GB758172A (en)

Also Published As

Publication number Publication date
BE532339A (en) 1958-01-31
DE1041963B (en) 1958-10-30

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