m-Chloroperbenzoic acid → 2-({[5-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfinyl)-1,3-oxazole

HRID 1511518Notes

Reaction equation

HRID 1511518 reaction equation
[F:1][CH:2]([F:21])[O:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[CH2:14][S:15][C:16]1[O:17][CH:18]=[CH:19][N:20]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[F:21][CH:2]([F:1])[O:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([C:10]([F:12])([F:13])[F:11])[C:5]=1[CH2:14][S:15]([C:16]1[O:17][CH:18]=[CH:19][N:20]=1)=[O:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 462224072-({[5-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole

Product 1

HCID 462224082-({[5-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfinyl)-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon, 2-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole (2.00 g, 6 mmol) is initially charged in 333 ml of dichloromethane. With stirring and ice-cooling, 3-chloroperbenzoic acid (1.362 g, 6 mmol, 77% pure) is then added a little at a time, and the mixture is stirred at 0° C. for a further 6 hours. For work-up, the reaction mixture is extracted twice with 2-molar sodium hydroxide solution and then washed with water and finally with saturated NaCl solution. The combined organic phases are dried over magnesium sulfate, filtered off and concentrated. The crude product is purified chromatographically (heptane:ethyl acetate, gradient 10:0 to 6:4). This gives 1.98 g of product (89.7% of theory).

Workup

  1. temperatureice-cooling
  2. stirringthe mixture is stirred at 0° C. for a further 6 hours
  3. extractionFor work-up, the reaction mixture is extracted twice with 2-molar sodium hydroxide solution
  4. washwashed with water and finally with saturated NaCl solution
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated
  8. customThe crude product is purified chromatographically (heptane:ethyl acetate, gradient 10:0 to 6:4)

Sources & evidence

ORD record
ord-4f059c4c43454e9f8405d238d2d055f8
Source dataset
uspto-grants-2012_07
Patent number
US08216973B2

Reaction notes

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