Methyl chloroformate → 3-(2-Methoxycarbonylaminoethoxy)-5-phenylisoxazole

HRID 612933Notes

Reaction equation

HRID 612933 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8][N:7]=1.Cl[C:18]([O:20][CH3:21])=[O:19].C(N(CC)CC)C>O1CCCC1>[CH3:21][O:20][C:18]([NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8][N:7]=1)=[O:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 98595963-(2-Aminoethoxy)-5-phenylisoxazole hydrochloride

Product 1

HCID 195964593-(2-Methoxycarbonylaminoethoxy)-5-phenylisoxazoleYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

3-(2-Aminoethoxy)-5-phenylisoxazole hydrochloride (240 mg) was suspended in anhydrous tetrahydrofuran (5 ml), and the suspension was cooled to 5° C. Then, methyl chloroformate (113 mg) and triethylamine (243 mg) were added thereto, and the resulting mixture was stirred at the same temperature for 30 minutes. At the end of this time, the reaction mixture was added to ice-cold water (40 ml) and extracted with ethyl acetate (40 ml×2). Then, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The crystals thus obtained were recrystallized from a mixture of ethyl acetate and ether to obtain the title compound (233 mg, 89%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate (40 ml×2)
  2. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe crystals thus obtained
  6. customwere recrystallized from a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-6e6ee5606e644568b7276bb89beb4850
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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