NO944238L - Process for the preparation of hydroxyalkanecarboxylic acid amides - Google Patents

Process for the preparation of hydroxyalkanecarboxylic acid amides

Info

Publication number
NO944238L
NO944238L NO944238A NO944238A NO944238L NO 944238 L NO944238 L NO 944238L NO 944238 A NO944238 A NO 944238A NO 944238 A NO944238 A NO 944238A NO 944238 L NO944238 L NO 944238L
Authority
NO
Norway
Prior art keywords
acid
hydroxyalkanecarboxylic
carbon atoms
general formula
moles
Prior art date
Application number
NO944238A
Other languages
Norwegian (no)
Other versions
NO944238D0 (en
Inventor
Stefan Scholz
Michael Harre
Hans-Jorg Vidic
Gunter Neef
Gerald Kirsch
Original Assignee
Schering Ag
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 Schering Ag filed Critical Schering Ag
Publication of NO944238D0 publication Critical patent/NO944238D0/en
Publication of NO944238L publication Critical patent/NO944238L/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines

Landscapes

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

Abstract

Det er beskrevet en fremgangs- måte for fremstilling av hydroksyalkan- karboksylsyreamider av generell formel I HO-C -H, -CON \ (D hvori n betegner et helt tall på l til 20 og RI °9 ^2 betegner alkylgrupper med maksimalt 8 karbonatomer, eller beteg- ner sammen en alkylengruppe med 4 til 8 karbonatomer som eventuelt er avbrutt av et oksygenatom eller et nitrogen- atom, fra hydroksyalkankarboksylsyrer av generell formel II HO-CnH, -COOH (II) hvori n har den ovenfor angitte betydning, og aminer av generell formel III HN \ (III) hvori R! og R2 har den ovenfor angitte betyd- ning, som er kjennetegnet ved at hydroksy- alkankarboksylsyren i en enkarsreaksjon oppvarmes under tilbakeløpskjøling med 10 til 30 mol acetylklorid pr. mol syre, det overskytende acetylklorid etter endt acetylering avdestilleres, residuet oppvarmes under tilbakeløps- kjøling med 1,5 til 5 mol tionylklorid pr. mol syre, tionylkloridet fjernes ved destillasjon etter endt syreklorid- dannelse, residuet oppløses i en di- alkyleter med 4 til 8 karbonatomer, den erholdte løsning innføres proporsjonalt i en vandig løsning av aminet avkjølt til O "C til 10 °C, og etter endt amid- dannelse avspaltes acetatgruppen ved behandling med vandig natriumhydroksid- løsning ved en reaksjonstemperatur på 10 'C til 30 "C.There is disclosed a process for preparing hydroxyalkanecarboxylic acid amides of general formula I HO-C-H, -CON \ (D wherein n represents an integer of 1 to 20 and R 1 9 9 2 represents alkyl groups having a maximum of 8 carbon atoms , or together represents an alkylene group of 4 to 8 carbon atoms optionally interrupted by an oxygen atom or a nitrogen atom, from hydroxyalkanecarboxylic acids of general formula II HO-CnH, -COOH (II) wherein n is as defined above, and amines of general formula III HN \ (III) wherein R 1 and R 2 are as defined above, characterized in that the hydroxyalkanecarboxylic acid is heated in reflux with refluxing with 10 to 30 moles of acetyl chloride per mole of acid, the excess acetyl chloride after acetylation has been distilled off, the residue is heated under reflux with 1.5 to 5 moles of thionyl chloride per mole of acid, the thionyl chloride is removed by distillation after acid chloride formation is formed, the residue is dissolved in a dialkyl ether having 4 to 8 carbon atoms, the solution obtained is proportionally introduced into an aqueous solution of the amine cooled to 0 ° C to 10 ° C, and upon completion of amide formation, the acetate group is decomposed by treatment with aqueous sodium hydroxide solution at a reaction temperature of 10 'C to 30' C

NO944238A 1992-05-07 1994-11-07 Process for the preparation of hydroxyalkanecarboxylic acid amides NO944238L (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19924214895 DE4214895A1 (en) 1992-05-07 1992-05-07 Process for the preparation of hydroxyalkane carboxamides
PCT/DE1993/000413 WO1993022278A1 (en) 1992-05-07 1993-05-05 Process for producing hydroxyalkane carboxylic acid amides

Publications (2)

Publication Number Publication Date
NO944238D0 NO944238D0 (en) 1994-11-07
NO944238L true NO944238L (en) 1994-11-07

Family

ID=6458253

Family Applications (1)

Application Number Title Priority Date Filing Date
NO944238A NO944238L (en) 1992-05-07 1994-11-07 Process for the preparation of hydroxyalkanecarboxylic acid amides

Country Status (9)

Country Link
EP (1) EP0639177A1 (en)
JP (1) JPH07506819A (en)
AU (1) AU4259493A (en)
CA (1) CA2127292A1 (en)
DE (1) DE4214895A1 (en)
FI (1) FI945181A0 (en)
HU (1) HUT68198A (en)
NO (1) NO944238L (en)
WO (1) WO1993022278A1 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4420736C1 (en) * 1994-06-15 1995-08-10 Henkel Kgaa New pseudo-ceramide cpds.
DE4427837A1 (en) * 1994-08-05 1996-02-08 Hoechst Ag Process for the preparation of O-acylglycolic acid anilides
DE19525098A1 (en) * 1995-07-10 1997-01-16 Hoechst Ag Process for the preparation of hydroxycarboxylic acid anilides
US7541489B2 (en) 2004-06-30 2009-06-02 Sabic Innovative Plastics Ip B.V. Method of making halophthalic acids and halophthalic anhydrides
DE102008017213B4 (en) * 2008-04-04 2012-08-09 Clariant International Limited Continuous process for the preparation of amides of aliphatic hydroxycarboxylic acids
WO2010108817A1 (en) 2009-03-26 2010-09-30 Basf Se Method for producing n,n`-lactic acid dialkylamide using ionic liquids
WO2010108814A1 (en) 2009-03-26 2010-09-30 Basf Se Method for producing n,n`-lactic acid dialkylamide under pressure

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB868556A (en) * 1957-05-02 1961-05-17 Hoechst Ag Analeptically active ª--hydroxy-and ª--acyloxy-butyric acid alkyl-amides and a process for their manufacture
DE3905325A1 (en) * 1989-02-17 1990-09-06 Schering Ag HYDROXYALKANCARBONE ACID DERIVATIVES, THEIR PREPARATION AND USE

Also Published As

Publication number Publication date
DE4214895A1 (en) 1993-11-11
CA2127292A1 (en) 1993-11-11
FI945181A (en) 1994-11-03
FI945181A0 (en) 1994-11-03
EP0639177A1 (en) 1995-02-22
JPH07506819A (en) 1995-07-27
AU4259493A (en) 1993-11-29
NO944238D0 (en) 1994-11-07
WO1993022278A1 (en) 1993-11-11
HU9401335D0 (en) 1994-08-29
HUT68198A (en) 1995-05-29

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