Potassium Carbonate → Phenyl 5-phenylisoxazol-3-ylcarbamate

HRID 871429Notes

Reaction equation

HRID 871429 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-7bb5abc5317046ba8724ecc3a94da735
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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