Sodium → HCID 22768158, compound

HRID 461352Notes

Reaction equation

HRID 461352 reaction equation
[CH3:1][O-].[Na+].[Na].[C:5]([C:9]1[O:13][N:12]=[C:11]([NH:14][C:15](=[O:18])[O:16][CH3:17])[CH:10]=1)([CH3:8])([CH3:7])[CH3:6]>CO>[CH3:1][N:14]([C:11]1[CH:10]=[C:9]([C:5]([CH3:8])([CH3:6])[CH3:7])[O:13][N:12]=1)[C:15](=[O:18])[O:16][CH3:17]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 13309592Methyl 5-tert-butyl-1,2-oxazol-3-ylcarbamate

Product 1

HCID 22768158HCID 22768158, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the sodium methoxide obtained by mixing sodium (1.57 g) with anhydrous methanol (45 ml), methyl N-(5-t-butyl-3-isoxazolyl)carbamate (12.88 g) is added. The resultant mixture is stirred at room temperature for 10 minutes, and the methanol is evaporated under reduced pressure. The residue is mixed with anhydrous benzene (100 ml) and dimethyl sulfate (8.61 g). The resultant mixture is stirred for 1 hour and refluxed for 1 hour. After cooling, the precipitate is filtered off. The organic layer is washed with an aqueous saturated solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate, and the solvent is evaporated. The residue is distilled to give methyl N-methyl-N-(5-t-butyl-3-isoxazolyl)carbamate (11.45 g) as a distillate boiling at 84.0° to 87.0° C/0.55 mm Hg.

Workup

  1. additionis added
  2. customthe methanol is evaporated under reduced pressure
  3. additionThe residue is mixed with anhydrous benzene (100 ml) and dimethyl sulfate (8.61 g)
  4. temperaturerefluxed for 1 hour
  5. temperatureAfter cooling
  6. filtrationthe precipitate is filtered off
  7. washThe organic layer is washed with an aqueous saturated solution of sodium bicarbonate and water in order
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent is evaporated
  10. distillationThe residue is distilled

Sources & evidence

ORD record
ord-4c450a4305974a99b23f6a7e6c9fec02
Source dataset
uspto-grants-1977_12
Patent number
US04062861

Reaction notes

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