Water → Phenyl 5-methylisoxazol-3-ylcarbamate

HRID 1433407Notes

Reaction equation

HRID 1433407 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1.[C:8](Cl)(=[O:16])[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>O1CCCC1.N1C=CC=CC=1>[CH3:7][C:5]1[O:4][N:3]=[C:2]([NH:1][C:8](=[O:16])[O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 15891Phenyl chloroformateHCID 661723-Amino-5-methylisoxazole

Product 1

HCID 4519264Phenyl 5-methylisoxazol-3-ylcarbamateYield 68%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-5-methylisoxazole (1.00 g) purchased from Aldrich Co. was dissolved in tetrahydrofuran (20 ml) and pyridine (1.5 ml), and after cooling to 0° C. under a nitrogen atmosphere, phenyl chlorocarbonate (1.4 ml) was added and the mixture was stirred at room temperature for 2 hours. Water was added, extraction was performed twice with ethyl acetate, and then the organic layers were combined, washed with water and saturated brine in that order, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was triturated with diethyl ether and n-hexane to obtain the title compound (1.54 g) (68% yield).

Workup

  1. extractionextraction
  2. washwashed with water and saturated brine in that order
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was triturated with diethyl ether and n-hexane

Sources & evidence

ORD record
ord-154d41532f254b69ad4203dbc747c589
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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