m-Chloroperbenzoic acid → HCID 59504634, compound

HRID 2400591Notes

Reaction equation

HRID 2400591 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([S:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)[N:16]=2)[CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:36].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([C:27]([F:29])([F:30])[F:28])=[O:36])=[CH:22][CH:21]=3)[N:16]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59504716HCID 59504716, compound

Product 1

HCID 59504634HCID 59504634, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mechanically stirred solution of 5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-3-{4-[(trifluoromethyl)sulfanyl]phenyl}-1,2,4-oxadiazole (Example 105, 570 mg, 1.32 mmol) in dichloromethane (215 mL) was added 3-chloroperoxybenzoic acid (408 mg, 1.66 mmol) at a temperature of 0° C. The reaction mixture was stirred over night at the same temperature. Then saturated aqueous sodium bicarbonate solution (80 mL) was added, and the mixture was extracted with dichloromethane (3×30 mL). The combined organic extracts were dried over anhydrous sodium sulfate. After filtration and evaporation of the solvent, the title compound was obtained as a white solid after purification by MPLC (silica, cyclohexane/ethyl acetate 4:1) (346 mg, 59%): 1H NMR (400 MHz, DMSO-d6) 8.38 (d, 2H), 8.11 (d, 2H), 7.18 (d, 2H), 7.12 (d, 2H), 6.92 (s, 1H), 5.43 (s, 2H), 2.32 (s, 3H), 2.27 (s, 3H); ES-MS m/z 447, HPLC RT (Method E) 2.44 min.

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×30 mL)
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationAfter filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-97cedc69eaff4aa7970373868fd94999
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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