m-Chloroperbenzoic acid → HCID 44329885, compound

HRID 363462Notes

Reaction equation

HRID 363462 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH2:14][F:15])([CH2:12][F:13])[CH:9]=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:7]=2[CH:22]=1)#[N:2].ClC1C=CC=C(C(OO)=[O:31])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH2:14][F:15])([CH2:12][F:13])[CH:9]=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N+:17]=3[O-:31])[C:7]=2[CH:22]=1)#[N:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 21831301HCID 21831301, compound

Product 1

HCID 44329885HCID 44329885, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 3 ml of methylene chloride was dissolved 80 mg of 6-cyano-2,2-bisfluoromethyl-4-(2-pyridyl)-2H-1-benzopyran and 75.7 mg of m-chloroperbenzoic acid (70%) was added thereto with stirring under ice-cooling. The mixture was stirred at room temperature for 15 hours. After addition of 28 mg of m-chloroperbenzoic acid (70%), the mixture was further stirred for 19 hours. Sodium bicarbonate solution was added thereto and the mixture was extracted with methylene chloride. After the organic layer was washed with water and dried, the solvent was distilled off. The resultant residue was purified using silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain 30 mg of 2-(6-cyano-2,2-bisfluoromethyl-2H-1-benzopyran-4-yl)pyridine N-oxide represented by the following formula having a melting point of 204°-207° C. NMR(CDCl3)δ: 4.63(4H,d), 5.89(1H,s), 6.82-7.62(6H,m), 8.13-8.47(1H,m). MS m/z: 314(M+) ##STR50##

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringThe mixture was stirred at room temperature for 15 hours
  4. stirringthe mixture was further stirred for 19 hours
  5. extractionthe mixture was extracted with methylene chloride
  6. washAfter the organic layer was washed with water
  7. customdried
  8. distillationthe solvent was distilled off
  9. customThe resultant residue was purified

Sources & evidence

ORD record
ord-ec822a9b4680495fb702d8bd20aa937b
Source dataset
uspto-grants-1999_02
Patent number
US05874446

Reaction notes

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