Sodium Hydroxide → 3-Isopropyl-1,2,4-oxadiazole-5-carboxylic acid

HRID 1409317Notes

Reaction equation

HRID 1409317 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([C:9]([O:11]CC)=[O:10])[O:6][N:5]=1)([CH3:3])[CH3:2].[OH-].[Na+]>CCO.O>[CH:1]([C:4]1[N:8]=[C:7]([C:9]([OH:11])=[O:10])[O:6][N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 534046373-Isopropyl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester

Product 1

HCID 232010263-Isopropyl-1,2,4-oxadiazole-5-carboxylic acidYield 102.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3-isopropyl-1,2,4-oxadiazole-5-carboxylate (10.42 mmol, 1.919 g) was dissolved in EtOH (20 ml). Sodium hydroxide pellets (12.50 mmol, 0.500 g) were dissolved in cold water (10 ml) and solution slowly added. The resulting solution was heated at 60° C. for 1.5 h. EtOH was removed under vacuum. The residue was diluted with tert-butyl methyl ether. The mixture was acidified under cold conditions by adding 2 N HCl solution. The mixture was stirred overnight and washed with DCM. Water phase was evaporated precipitating the product. 1.673 g of the title compound was obtained. 1H-NMR (400 MHz, D2O): δ 1.33 (d, 6H), 3.10-3.25 (m, 1H).

Workup

  1. additionsolution slowly added
  2. customEtOH was removed under vacuum
  3. additionThe residue was diluted with tert-butyl methyl ether
  4. additionby adding 2 N HCl solution
  5. washwashed with DCM
  6. customWater phase was evaporated
  7. customprecipitating the product

Sources & evidence

ORD record
ord-9e595cb122c241f99bd546075d4fb8e3
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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