Hydrochloric Acid → HCID 4380357, compound

HRID 461349Notes

Reaction equation

HRID 461349 reaction equation
[C:1](=[O:6])([O:4][CH3:5])OC.C[O-].[Na+].[NH2:10][C:11]1[CH:15]=[C:14]([CH3:16])[O:13][N:12]=1.Cl>C(OCC)(=O)C.O>[CH3:16][C:14]1[O:13][N:12]=[C:11]([NH:10][C:1](=[O:6])[O:4][CH3:5])[CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 661723-Amino-5-methylisoxazoleHCID 10942334Sodium Methoxide

Product 1

HCID 4380357HCID 4380357, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dimethyl carbonate (2.38 g) and sodium methoxide (0.30 g) are added to 3-amino-5-methylisoxazole (0.49 g), and the resultant mixture is stirred at 100° C for 3 hours. After cooling, the reaction mixture is combined with water (15 ml), adjusted to pH 1 with a small amount of c. hydrochloric acid and shaken twice with ethyl acetate. The organic layer is washed with water, dried over anhydrous sodium sulfate and evaporated to remove the solvent. The resulting light yellow crystals (0.52 g) are chromatographed on a column of silica gel, whereby methyl N-(5-methyl-3-isoxazolyl)carbamate is obtained as crystals melting at 136.0° to 137.0° C.

Workup

  1. temperatureAfter cooling
  2. washThe organic layer is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto remove the solvent
  6. customThe resulting light yellow crystals (0.52 g) are chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-b71b8159f91a407d8f07a1cb46e52643
Source dataset
uspto-grants-1977_12
Patent number
US04062861

Reaction notes

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