Potassium Carbonate → Phenyl 5-phenylisoxazol-3-ylcarbamate

HRID 1917828Notes

Reaction equation

HRID 1917828 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([NH2:12])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](=[O:16])([O-])[O-:14].[K+].[K+]>O1CCCC1>[C:1]1([C:7]2[O:11][N:10]=[C:9]([NH:12][C:13](=[O:16])[O:14][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 36207925-Phenyl-1,2-oxazol-3-amine

Product 1

HCID 59394374Phenyl 5-phenylisoxazol-3-ylcarbamateYield 160.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Phenylisoxazol-3-amine (428 mg, 2.67 mmol) in tetrahydrofuran (4.8 mL) was treated with potassium carbonate (481 mg, 3.47 mmol) and phenyl choloroformate (0.67 mL, 5.3 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was filtered through a celite pad, washed with ethyl acetate and concentrated to dryness. The residue was taken into chloroform, washed with brine, and the organics dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (hexane/ethyl acetate 8:2) to give phenyl 5-phenylisoxazol-3-ylcarbamate (599 mg, 80%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.92 (bs, 1H), 7.78 (d, 2H), 7.45 (m, 6H), 7.26 (m, 2H), 7.12 (s, 1H); LC-MS (ESI) m/z 281 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. washwashed with ethyl acetate
  3. concentrationconcentrated to dryness
  4. washwashed with brine
  5. dry with materialthe organics dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate 8:2)

Sources & evidence

ORD record
ord-943be0e3254043adb86436c508ea127c
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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