m-Chloroperbenzoic acid → HCID 21862862, compound

HRID 1415841Notes

Reaction equation

HRID 1415841 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=2)[N:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13](=[O:16])(=[O:15])[NH2:14])=[CH:9][CH:8]=2)[CH:6]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:24])=[O:33])=[CH:19][CH:18]=2)[N:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13](=[O:16])(=[O:15])[NH2:14])=[CH:9][CH:8]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9906806HCID 9906806, compound

Product 1

HCID 21862862HCID 21862862, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

0.35 g (1.0 mmol) of 4-methyl-2-(4-methylthiophenyl)-1-(4-sulfamoylphenyl)pyrrole (prepared as described in Example 66) was dissolved in 50 ml of chloroform, and 0.27 g (1.1 mmol) of 70% m-chloroperbenzoic acid was added to the resulting solution in several portions, whilst ice-cooling, after which the mixture was stirred for 1 hour, whilst ice-cooling. The reaction mixture was then diluted with chloroform and was washed with a 10% w/v aqueous solution of sodium thiosulfate and with a saturated aqueous solution of sodium hydrogencarbonate twice each, in that order. The organic layer was then dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue thus obtained was applied to a silica gel chromatography column and eluted with a 95:5 by volume mixture of methylene chloride and methanol, to give 0.23 g (yield 63%) of the title compound as a pale orange-colored powder, melting at 222-226° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. washwas washed with a 10% w/v aqueous solution of sodium thiosulfate and with a saturated aqueous solution of sodium hydrogencarbonate twice each, in that order
  4. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue thus obtained
  7. washeluted with a 95:5 by volume mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-a1d4d3ab64014f4cb0e1ced7e0766b87
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

Loading…