Water → Phenyl (3-methylisoxazol-5-yl)carbamate

HRID 853277Notes

Reaction equation

HRID 853277 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH3:7])[CH: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:4]1[CH: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)[O:6][N:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 15891Phenyl chloroformateHCID 845905-Amino-3-methylisoxazole

Product 1

HCID 22936635Phenyl (3-methylisoxazol-5-yl)carbamateYield 20%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-3-methylisoxazole (1 g) purchased from Aldrich Co. was dissolved in tetrahydrofuran (40 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 1.5 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 recrystallized from ethyl acetate and n-hexane to obtain the title compound (450 mg, 20% 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 recrystallized from ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-40a78788d50c47679e9a4b5618556bac
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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