Chloroform → HCID 86720750, compound

HRID 2167699Notes

Reaction equation

HRID 2167699 reaction equation
C(Cl)(Cl)Cl.[CH3:5][C:6]1[N:7]=[CH:8][C:9]([CH3:15])([N+:12]([O-:14])=[O:13])[CH2:10][CH:11]=1.C(N)(N)=[O:17].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O>[CH3:5][C:6]1[N+:7]([O-:17])=[CH:8][C:9]([CH3:15])([N+:12]([O-:14])=[O:13])[CH2:10][CH:11]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 86720751HCID 86720751, compound

Product 1

HCID 86720750HCID 86720750, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a chloroform (10 mL) solution of 2,5-dimethyl-5-nitropyridine (1.2 g), under ice cooling in a nitrogen atmosphere, carbamide peroxide (1.9 g) and trifluoroacetic anhydride (2.3 mL) were added dropwise, and the resultant was stirred for 30 minutes under ice cooling and then stirred at room temperature for 13 hours. Water was added to the reaction mixture, followed by extraction with chloroform. The obtained organic layer was washed with a 10% aqueous sodium thiosulfate solution and then dried over sodium sulfate, and the desiccant was filtered off. Then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (OH-type silica gel; chloroform/ethyl acetate-gradient elution=100/0→0/100) to obtain the title compound (1.0 g) as a yellow solid.

Workup

  1. stirringstirred at room temperature for 13 hours
  2. extractionfollowed by extraction with chloroform
  3. washThe obtained organic layer was washed with a 10% aqueous sodium thiosulfate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationthe desiccant was filtered off
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (OH-type silica gel; chloroform/ethyl acetate-gradient elution=100/0→0/100)

Sources & evidence

ORD record
ord-fc0d780bd6fb4834b8cd4c4dca110449
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

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