Sodium Hydroxide → HCID 70980262, compound

HRID 1409366Notes

Reaction equation

HRID 1409366 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]([O:15]CC)=[O:14])[N:9]=2)=[N:3]1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]([OH:15])=[O:14])[N:9]=2)=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70981759HCID 70981759, compound

Product 1

HCID 70980262HCID 70980262, compoundYield 133.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-(1,5-dimethyl-1H-pyrazol-3-yl)-1,2,4-oxadiazole-3-carboxylate (1.206 mmol, 0.285 g) was dissolved in ethanol (7 ml) and cooled to 0° C. with an ice bath. NaOH 1 M solution (3 ml) was added, the ice bath was removed and the mixture was heated to 60° C. for 1.5 h. Ethanol was evaporated and the residue was diluted with MTBE. The mixture was again cooled with an ice bath and acidified with 2 M HCl. The mixture was warmed to RT and stirred overnight. Water, MTBE and DCM were added, but the precipitate did not dissolve. The organic phase and the water phase were combined and evaporated. 0.336 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 2.27 (s, 3H), 4.16 (s, 3H), 7.01 (s, 1H).

Workup

  1. customthe ice bath was removed
  2. temperaturethe mixture was heated to 60° C. for 1.5 h
  3. customEthanol was evaporated
  4. additionthe residue was diluted with MTBE
  5. temperatureThe mixture was again cooled with an ice bath
  6. temperatureThe mixture was warmed to RT
  7. additionWater, MTBE and DCM were added
  8. dissolutionthe precipitate did not dissolve
  9. customevaporated

Sources & evidence

ORD record
ord-c12ded43bee74e7387272e7cea5be1fd
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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