Water → 3-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline

HRID 230845Notes

Reaction equation

HRID 230845 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8](=[NH:11])[NH:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:14](OC)(=O)[CH3:15].O>O1CCCC1>[CH3:14][C:15]1[O:10][N:9]=[C:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[NH2:1])[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6584Methyl AcetateHCID 24758Sodium hydrideHCID 178513310HCID 178513310, compound

Product 1

HCID 114238693-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of Intermediate 18 (5.3 g) in dry tetrahydrofuran (50 ml) was added 4 Å molecular sieves, followed by sodium hydride (60% dispersion in mineral oil; 1.5 g) and the mixture heated at 65° C. for 30 min. After cooling to room temperature methyl acetate (2.8 ml) was added and the mixture heated under reflux for 16 h. After cooling to 20° C. the mixture was added to water (100 ml) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with dichloromethane to give the title compound as a white solid (4.0 g).

Workup

  1. additionwas added
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 16 h
  4. temperatureAfter cooling to 20° C. the mixture
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-2e4fa84e52b04087a56901db2ef8c3c9
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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