Sodium Hydroxide → HCID 63383100, compound

HRID 1409369Notes

Reaction equation

HRID 1409369 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[O:10][N:9]=[C:8]([C:11]([O:13]CC)=[O:12])[N:7]=2)=[N:2]1.[OH-].[Na+]>C(O)C>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[O:10][N:9]=[C:8]([C:11]([OH:13])=[O:12])[N:7]=2)=[N:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 63383281HCID 63383281, compound

Product 1

HCID 63383100HCID 63383100, compoundYield 155.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-(isoxazol-3-yl)-1,2,4-oxadiazole-3-carboxylate (1.893 mmol, 0.396 g) was dissolved in ethanol (5 ml) and cooled to 0° C. with an ice bath. NaOH 1 M solution (4 ml) was slowly added and the mixture was heated to 60° C. for 3 h. Ethanol was evaporated and the residue was diluted with MTBE. The mixture was cooled to 0° C. and acidified by adding 2 M HCl. The mixture was stirred at RT overnight. Water was added and the phases were separated and the water phase was evaporated. 0.533 g of the title compound was obtained. 1H-NMR (400 MHz, D2O): δ 6.68 (d, 1H), 8.65 (d, 1H).

Workup

  1. temperaturethe mixture was heated to 60° C. for 3 h
  2. customEthanol was evaporated
  3. additionthe residue was diluted with MTBE
  4. temperatureThe mixture was cooled to 0° C.
  5. additionby adding 2 M HCl
  6. additionWater was added
  7. customthe phases were separated
  8. customthe water phase was evaporated

Sources & evidence

ORD record
ord-be299ca7df6a4807bbf789aa0c3c3b5c
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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