m-Chloroperbenzoic acid → HCID 86656397, compound

HRID 1948511Notes

Reaction equation

HRID 1948511 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH:27]=[CH2:28])=[CH:23][C:22]=4[C:29]([F:32])([F:31])[F:30])[N:17]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:41])C=1>C(Cl)Cl>[O:41]1[CH2:28][CH:27]1[C:24]1[CH:25]=[CH:26][C:21]([C:18]2[N:17]=[C:16]([C:10]3[O:9][N:8]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:11]=3[C:12]([F:13])([F:14])[F:15])[O:20][N:19]=2)=[C:22]([C:29]([F:32])([F:31])[F:30])[CH:23]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86656396HCID 86656396, compound

Product 1

HCID 86656397HCID 86656397, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-3-(2-(trifluoromethyl)-4-vinylphenyl)-1,2,4-oxadiazole (56 mg, 0.124 mmol) in DCM (5 mL) was added mCPBA (64.2 mg, 0.372 mmol). The reaction mixture was stirred overnight. The reaction mixture was diluted with dichloromethane and washed with 1N NaOH. The organic layer was dried with MgSO4, filtered, and concentrated to yield 50 mg of 3-(4-(oxiran-2-yl)-2-(trifluoromethyl)phenyl)-5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazole. MS (m+1)=468. HPLC Peak RT=2.12 minutes (Analytical Method B).

Workup

  1. washwashed with 1N NaOH
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2268f534cfa34b1ea9235d6fc5273dd8
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

Loading…