m-Chloroperbenzoic acid → HCID 86634873, compound

HRID 2366388Notes

Reaction equation

HRID 2366388 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].ClC1C=C(C=CC=1)C(OO)=[O:26]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)/[C:12]#[N+:13][O-:26])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 5879565HCID 5879565, compound

Product 1

HCID 86634873HCID 86634873, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 30 (266 mg) was dissolved in anhydrous dichloromethane (50 mL). m-chloroperoxybenzoic acid (266 mg) was added dropwise to the solution under stirring in an ice bath. The mixture was stirred for about 15 minutes under argon which was fed by means of a separately provided balloon filled with argon. The mixture was returned to room temperature, followed by stirring for 3 hours. The reaction mixture was extracted with purified water and chloroform. The organic layer was washed with brine, and the washed organic layer was dried over sodium sulfate anhydrate. The solvent was evaporated to dryness. The residue was purified by silica gel column chromatography (chloroform-methanol), to thereby yield the target product (yield: 265 mg, 94%).

Workup

  1. stirringThe mixture was stirred for about 15 minutes under argon which
  2. additionfilled with argon
  3. customwas returned to room temperature
  4. stirringby stirring for 3 hours
  5. extractionThe reaction mixture was extracted with purified water and chloroform
  6. washThe organic layer was washed with brine
  7. dry with materialthe washed organic layer was dried over sodium sulfate anhydrate
  8. customThe solvent was evaporated to dryness
  9. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-0f4337b2067247b98243a864e9bb5a8d
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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