Trifluoroacetic anhydride → 3-[5-(3,4-Dimethoxy-5-nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-trifluoromethyl-pyridine 1-oxide

HRID 1401288Notes

Reaction equation

HRID 1401288 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14]2[O:18][C:17]([C:19]3[C:20]([C:25]([F:28])([F:27])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:16][N:15]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9][CH3:10].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:32]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14]2[O:18][C:17]([C:19]3[C:20]([C:25]([F:28])([F:27])[F:26])=[N+:21]([O-:32])[CH:22]=[CH:23][CH:24]=3)=[N:16][N:15]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 670370412-(3,4-Dimethoxy-5-nitrophenyl)-5-(2-(trifluoromethyl)pyridin-3-yl)-1,3,4-oxadiazole

Product 1

HCID 670369683-[5-(3,4-Dimethoxy-5-nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-trifluoromethyl-pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-[5-(3,4-dimethoxy-5-nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-trifluoromethyl-pyridine (0.45 g, 1.13 mmol) in dichloromethane (10 mL)) cooled in an ice-water bath was added urea hydrogen peroxide complex (0.23 g, 2.45 mmol) in one portion followed by trifluoroacetic anhydride (0.47 g, 2.24 mmol) dropwise. The resulting mixture was allowed to stir at room temperature overnight and then the insoluble material was filtered off. The filtrate was washed with water and brine, then dried over anhydrous sodium sulphate, filtered and evaporated to leave an off-white solid. Recrystallisation from ethanol afforded 3-[5-(3,4-dimethoxy-5-nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-trifluoromethyl-pyridine 1-oxide, 0.39 g (83%).

Workup

  1. additionwas added urea hydrogen peroxide complex (0.23 g, 2.45 mmol) in one portion
  2. filtrationthe insoluble material was filtered off
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customto leave an off-white solid
  8. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-44bcdb8a7329466296a0272da41692c6
Source dataset
uspto-grants-2014_12
Patent number
US08907099B2

Reaction notes

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