p-Toluenesulfonic acid → HCID 15018904, compound

HRID 344596Notes

Reaction equation

HRID 344596 reaction equation
[CH2:1]([C:4]1[C:9]([OH:10])=[C:8]([Cl:11])[CH:7]=[C:6]([F:12])[C:5]=1[N:13]1[C:17](=[O:18])[C:16]2[CH2:19][CH2:20][CH2:21][CH2:22][C:15]=2[C:14]1=[O:23])[CH:2]=[CH2:3].C1C=C(Cl)C=C(C(OO)=[O:32])C=1.CC1C=CC(S(O)(=O)=O)=CC=1>ClCCCl>[Cl:11][C:8]1[C:9]2[O:10][CH:2]([CH2:3][OH:32])[CH2:1][C:4]=2[C:5]([N:13]2[C:17](=[O:18])[C:16]3[CH2:19][CH2:20][CH2:21][CH2:22][C:15]=3[C:14]2=[O:23])=[C:6]([F:12])[CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 70297m-Chloroperbenzoic acidHCID 57180770HCID 57180770, compound

Product 1

HCID 15018904HCID 15018904, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 0.67 g of 19C and 475 mg of 80% MCPBA in 15 mL of 1,2-dichloroethane was heated on an oil bath at 70° C. for 2.5 hours. A few milligrams of PTSA was added, the mixture was cooled to room temperature, washed with a saturated aqueous solution of sodium sulfite, followed by a saturated aqueous solution of sodium bicarbonate, dried (Na2SO4), filtered and stripped of solvent. The residue was flash chromatographed on silica gel with a 40:60 v:v mixture of ethyl acetate and hexane as eluent, to give the title compound, as white crystals, m.p.: 193°-195° C.

Workup

  1. washwashed with a saturated aqueous solution of sodium sulfite
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customchromatographed on silica gel with a 40:60 v
  5. additionv mixture of ethyl acetate and hexane as eluent

Sources & evidence

ORD record
ord-ffd8046ecacd4cb8a145891a93fd7bda
Source dataset
uspto-grants-1991_10
Patent number
US05053071

Reaction notes

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