Potassium Carbonate → HCID 54334392, compound

HRID 1601418Notes

Reaction equation

HRID 1601418 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1([C:22]([F:25])([F:24])[F:23])[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:6]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:5]=2[O:4]1.ClC1C=CC=C(C(OO)=[O:36])C=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[F:27][C:2]([F:1])([F:26])[C:3]1([C:22]([F:24])([F:25])[F:23])[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=2[O-:36])[C:6]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:5]=2[O:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 21831312HCID 21831312, compound

Product 1

HCID 54334392HCID 54334392, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 4 ml of methylene chloride was dissolved 200 mg of 2,2-bistrifluoromethyl-6-nitro-4-(2-pyridyl)-2H-1-benzopyran and 210 mg of m-chloroperbenzoic acid (67%) was added thereto with stirring under ice-cooling. The mixture was stirred at room temperature for 14 hours. Potassium carbonate solution was added thereto and the mixture was extracted with methylene chloride. The organic layer was washed with water and dried. The solvent was distilled off and the resultant residue was purified using silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain 140 mg of 2-(2,2-bistrifluoromethyl-6-nitro-2H-1-benzopyran-4-yl)pyridine N-oxide represented by the following formula having a melting point of 208-210° C.

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringThe mixture was stirred at room temperature for 14 hours
  4. extractionthe mixture was extracted with methylene chloride
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationThe solvent was distilled off
  8. customthe resultant residue was purified

Sources & evidence

ORD record
ord-31041410851c4231beb09569b8396927
Source dataset
uspto-grants-1999_11
Patent number
US05977167

Reaction notes

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