Isobutyryl chloride → N-(5-t-butyl-3-isoxazolyl)isobutyramide

HRID 847651Notes

Reaction equation

HRID 847651 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[O:4][N:3]=1.[C:11](Cl)(=[O:15])[CH:12]([CH3:14])[CH3:13]>N1C=CC=CC=1>[C:7]([C:5]1[O:4][N:3]=[C:2]([NH:1][C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])[CH:6]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-

Product 1

HCID 13020366N-(5-t-butyl-3-isoxazolyl)isobutyramideYield 91.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-amino-5-t-butylisoxazole (2.80 g) in pyridine (10 ml) is dropwise added isobutyryl chloride (2.34 g) keeping the mixture below 10° C. The reaction mixture is stirred with cooling for 30 minutes and at room temperature for 1 hour and evaporated to remove the pyridine. The residue is mixed with 5% hydrochloric acid solution (40 ml) and shaken with methylene chloride. The methylene chloride layer is separated, washed with saturated aqueous sodium hydrogen carbonate and water, dried over anhydrous sodium sulfate and evaporated to remove the methylene chloride. The residue is chromatographed on a column of silica gel and recrystallized from n-hexane to give N-(5-t-butyl-3-isoxazolyl)isobutyramide (3.85 g) as colorless needles melting at 123.0° to 124.0° C.

Workup

  1. customthe mixture below 10° C
  2. customevaporated
  3. customto remove the pyridine
  4. additionThe residue is mixed with 5% hydrochloric acid solution (40 ml)
  5. stirringshaken with methylene chloride
  6. customThe methylene chloride layer is separated
  7. washwashed with saturated aqueous sodium hydrogen carbonate and water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated
  10. customto remove the methylene chloride
  11. customThe residue is chromatographed on a column of silica gel
  12. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-b48792f085f5446ab6ee7d03729abadf
Source dataset
uspto-grants-1981_10
Patent number
US04293328

Reaction notes

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