2,3-Dihydroxybutanedioic Acid → 3,4-Dihydroxy-1-(9Z)-9-octadecen-1-yl-2,5-pyrrolidinedione

HRID 1732199Notes

Reaction equation

HRID 1732199 reaction equation
[C:1]([OH:10])(=O)[CH:2]([CH:4]([C:6](O)=[O:7])[OH:5])[OH:3].[CH3:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH2:29]>C1(C)C=CC=CC=1>[CH2:28]([N:29]1[C:6](=[O:7])[CH:4]([OH:5])[CH:2]([OH:3])[C:1]1=[O:10])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]/[CH:20]=[CH:19]\[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 5356789Oleylamine2×

Product 1

HCID 704190063,4-Dihydroxy-1-(9Z)-9-octadecen-1-yl-2,5-pyrrolidinedione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

150 Parts of tartaric acid (obtained from Sargent Welch) is added to 173 parts of toluene and the mixture is heated with stirring to 100° C. 281 parts of Armeen O (essentially oleylamine, a product of Armak Chemicals, Chicago, Ill.) is added slowly and in small portions while the system is kept under nitrogen purge. After the addition of the Armeen O is completed the contents are heated to 130° C. at which temperature the water formed is removed by azeotroping, and collected. The temperature is then raised to 160° C., after no more water is collected and kept at about 160° C. for one hour under nitrogen purge to remove the toluene. The liquid residue is then filtered through diatomaceous earth to yield the desired N-oleyltartarimide. Analysis shows nitrogen content of 3.42% and hydroxyl content of 8.33%. The tartarimide can be expressed as ##STR4##

Workup

  1. temperaturethe mixture is heated
  2. addition) is added slowly and in small portions while the system
  3. custompurge
  4. additionAfter the addition of the Armeen O
  5. temperatureare heated to 130° C. at which temperature the water
  6. customformed
  7. customis removed
  8. customby azeotroping
  9. customcollected
  10. temperatureThe temperature is then raised to 160° C.
  11. customafter no more water is collected
  12. custompurge
  13. customto remove the toluene
  14. filtrationThe liquid residue is then filtered through diatomaceous earth

Sources & evidence

ORD record
ord-9863331ad27344a58a974cc5e7b27d8a
Source dataset
uspto-grants-1980_12
Patent number
US04237022

Reaction notes

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