m-Chloroperbenzoic acid → 4-(4-(2-Quinolinylmethylsulfinyl)phenoxymethyl)benzoic acid

HRID 2074028Notes

Reaction equation

HRID 2074028 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][S:12][C:13]1[CH:29]=[CH:28][C:16]([O:17][CH2:18][C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.ClC1C=CC=C(C(OO)=[O:38])C=1.C(=O)([O-])O.[K+]>ClC(Cl)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][S:12]([C:13]1[CH:29]=[CH:28][C:16]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=2)=[CH:15][CH:14]=1)=[O:38]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516893Potassium BicarbonateHCID 147741604-(4-(2-Quinolinylmethylthio)phenoxymethyl)benzoic acid

Product 1

HCID 147741614-(4-(2-Quinolinylmethylsulfinyl)phenoxymethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4-(4-(2-quinolinylmethylthio)phenoxymethyl)benzoic acid (4 mmol) in dichloroethane (50 ml) is stirred with m-chloroperbenzoic acid (4 mmol) and solid potassium hydrogen carbonate (1.0 g). The reaction is assayed by TLC and upon consumption of the starting thio compound, the mixture is filtered, washed with dilute aqueous sodium bisulfate, dried and evaporated to give 4-(4-(2-quinolinylmethylsulfinyl)phenoxymethyl)benzoic acid.

Workup

  1. customThe reaction is assayed by TLC and upon consumption of the starting thio compound
  2. filtrationthe mixture is filtered
  3. washwashed with dilute aqueous sodium bisulfate
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-7f0c09594cbe422bbf9826030b1c1972
Source dataset
uspto-grants-1990_04
Patent number
US04920132

Reaction notes

Loading…