Methyl Myristate → 3-Amino-5-tridecyl-1,2,4-oxadiazole

HRID 2081664

Reaction equation

HRID 2081664 reaction equation
[Na].[C:2]([NH:5][OH:6])([NH2:4])=[NH:3].OS(O)(=O)=O.CO[C:14](=O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(O)C>[NH2:3][C:2]1[N:4]=[C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])[O:6][N:5]=1

Participants

5

Reactant 3

HCID 31284Methyl MyristateHCID 5360545SodiumHCID 178513206HCID 178513206, compound

Product 1

HCID 197803343-Amino-5-tridecyl-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (1.6 g, 0.068 mol) was added to 4 Å molecular sieves (12 g) and ethanol (200 mL) under nitrogen. The mixture was stirred for 15 minutes, then hydroxyguanidine sulfate (9.32 g, 0.035 mol) added and the mixture stirred for 30 minutes. Methyltetradecanoate (1.43 g, 0.006 mol) was then added and the mixture refluxed for 1.5 hours, allowed to cool, filtered, and concentrated. The concentrate was partitioned between CH2Cl2 and water. The organic layer was washed with water and brine, dried with Na2SO4, filtered, concentrated, and triturated with hexane. The resulting solid was filtered, washed with hexane, and dried in vacuo to yield 0.23 g, m.p. 90°-91° C.

Workup

  1. stirringthe mixture stirred for 30 minutes
  2. temperaturethe mixture refluxed for 1.5 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was partitioned between CH2Cl2 and water
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customtriturated with hexane
  12. filtrationThe resulting solid was filtered
  13. washwashed with hexane
  14. customdried in vacuo
  15. customto yield 0.23 g, m.p. 90°-91° C.

Sources & evidence

ORD record
ord-629bdb03c25041b29434fa130bb592ee
Source dataset
uspto-grants-1993_02
Patent number
US05185358

Linked notes

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