Methanol → HCID 13292905, compound

HRID 436822Notes

Reaction equation

HRID 436822 reaction equation
[Na].[C:2]([C:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:15])[O:13][CH3:14])[O:8][N:7]=1)([CH3:5])([CH3:4])[CH3:3].[CH3:16]O>>[CH3:16][N:11]([C:9]1[O:8][N:7]=[C:6]([C:2]([CH3:5])([CH3:3])[CH3:4])[CH:10]=1)[C:12](=[O:15])[O:13][CH3:14]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 5360545SodiumHCID 13292894HCID 13292894, compound

Product 1

HCID 13292905HCID 13292905, compoundYield 91.8%

Procedure

To a solution of metallic sodium (0.42 g) in methanol (12 ml), a solution of methyl 3-t-butyl-5-isoxazolylcarbamate (3.47 g) in methanol (5.5 ml) is added, and the resultant mixture is stirred at room temperature for 10 minutes. The reaction mixture is evaporated under reduced pressure to remove the methanol. The residue is combined with benzene, which is then evaporated. The residue is again combined with benzene (27 ml), and dimethyl sulfate (2.32 g) is added dropwise. The resultant mixture is stirred at room temperature for 1 hour and then refluxed for 1 hour. After cooling, the reaction mixture is filtered to remove the precipitate. The filtrate is washed with aqueous sodium bicarbonate solution and then water, dried over anhydrous sodium sulfate and evaporated to remove the solvent. The residue is recrystallized from cyclohexanone to give methyl N-methyl-3-t-butyl-5-isoxazolylcarbamate (3.41 g) as crystals melting at 70.5° to 71.5° C. The yield is 91.8%.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. customto remove the methanol
  3. customis then evaporated
  4. additionis added dropwise
  5. temperaturerefluxed for 1 hour
  6. temperatureAfter cooling
  7. filtrationthe reaction mixture is filtered
  8. customto remove the precipitate
  9. washThe filtrate is washed with aqueous sodium bicarbonate solution
  10. dry with materialwater, dried over anhydrous sodium sulfate
  11. customevaporated
  12. customto remove the solvent
  13. customThe residue is recrystallized from cyclohexanone

Sources & evidence

ORD record
ord-01ceb47eee414a17868136e684649061
Source dataset
uspto-grants-1977_06
Patent number
US04028376

Reaction notes

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