m-Chloroperbenzoic acid → HCID 45254259, compound

HRID 1875860Notes

Reaction equation

HRID 1875860 reaction equation
[C:1]([C:5]1[S:6][C:7]([C:10]2[C:14]([S:15][CH3:16])=[C:13]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[N:12]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[Cl:31])[N:11]=2)=[N:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:40])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([C:5]1[S:6][C:7]([C:10]2[C:14]([S:15]([CH3:16])=[O:40])=[C:13]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:12]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[Cl:31])[N:11]=2)=[N:8][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 45256600HCID 45256600, compound

Product 1

HCID 45254259HCID 45254259, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-tert-Butyl-5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(methylthio)-1H-pyrazol-3-yl)-1,3,4-thiadiazole (Ia-2) (190 mg, 0.37 mmol) in CH2Cl2 (10 mL) was added m-CPBA (77% Max, 91 mg, 0.41 mmol). The reaction mixture was stirred for 1 hr at room temperature. Saturated NaHCO3 was added to the reaction mixture, then the organic extract was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was subjected to silica gel column chromatography (eluent: hexane/EtOAc=½) to obtain 148 mg (76%) of the title compound as a white solid.

Workup

  1. extractionthe organic extract
  2. dry with materialwas dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-920fc45b2c794dcd82b8f5a914be43f0
Source dataset
uspto-grants-2012_11
Patent number
US08309584B2

Reaction notes

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