Potassium Carbonate → 4-Chlorophenyl 5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-ylcarbamate

HRID 1918030Notes

Reaction equation

HRID 1918030 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:6]1[O:10][N:9]=[C:8]([NH2:11])[CH:7]=1)([CH3:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)=[O:22]>C1COCC1>[F:13][C:2]([F:1])([F:12])[C:3]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:21](=[O:22])[O:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH:7]=1)([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1390594-Chlorophenyl chloroformateHCID 56954313HCID 56954313, compound

Product 1

HCID 569541904-Chlorophenyl 5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-ylcarbamateYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-amine (123 mg, 0.63 mmol) in THF (2 mL) was treated with potassium carbonate (113 mg, 0.819 mmol) and p-chlorophenyl chloroformate (180 mg, 0.95 mmol). The reaction mixture was stirred at rt overnight. The mixture was filtered through a celite pad, washed with ethyl acetate and concentrated to dryness. The residue was taken into ethyl acetate, 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 4-chlorophenyl 5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-ylcarbamate (85 mg, 39%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.83 (brs, 1H), 7.38 (d, J=9 Hz, 2H), 7.15 (d, J=9 Hz, 2H), 6.82 (s, 1H), 1.59 (s, 6H); LC-MS (ESI) m/z 349 (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-f5b9433fe5bd449d84665914aa0e30cc
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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