m-Chloroperbenzoic acid → 3-(4-(Oxiran-2-yl)phenyl)-5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazole

HRID 1948465Notes

Reaction equation

HRID 1948465 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([CH:23]=[CH2:24])=[CH:19][CH:18]=4)[N:13]=3)[C:8]=2[CH2:25][CH2:26][CH3:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:36])C=1>C(Cl)Cl>[O:36]1[CH2:24][CH:23]1[C:20]1[CH:19]=[CH:18][C:17]([C:14]2[N:13]=[C:12]([C:9]3[C:8]([CH2:25][CH2:26][CH3:27])=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[O:11][N:10]=3)[O:16][N:15]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 583740935-(5-Phenyl-4-propylisoxazol-3-yl)-3-(4-vinylphenyl)-1,2,4-oxadiazole

Product 1

HCID 583741323-(4-(Oxiran-2-yl)phenyl)-5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(5-phenyl-4-propylisoxazol-3-yl)-3-(4-vinylphenyl)-1,2,4-oxadiazole (4.64 g, 12.97 mmol) in DCM (500 mL) was added m-CPBA (9 g, 52.2 mmol). The reaction mixture was stirred overnight at room temperature. Next, the reaction mixture was washed with 1N NaOH. The organic layer was dried with MgSO4, filtered, and concentrated to yield Preparation 1B. MS (m+1)=374. HPLC Peak RT=4.36 minutes (Analytical Method A).

Workup

  1. washNext, the reaction mixture was washed with 1N NaOH
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield

Sources & evidence

ORD record
ord-0fd2d1329be84b628a8f2dc163235bd6
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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