m-Chloroperbenzoic acid → N-[3-(3-Formyl-4-nitro-benzenesulfinyl)-phenyl]-benzenesulfonamide

HRID 390282Notes

Reaction equation

HRID 390282 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([S:12][C:13]2[CH:14]=[C:15]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])=[O:2].ClC1C=C(C(OO)=[O:37])C=CC=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH:1]([C:3]1[CH:4]=[C:5]([S:12]([C:13]2[CH:14]=[C:15]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=2)=[O:37])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])=[O:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid3×HCID 516892Sodium BicarbonateHCID 58625048N-[3-(3-Formyl-4-nitro-phenylsulfanyl)-phenyl]-benzenesulfonamide

Product 1

HCID 58625065N-[3-(3-Formyl-4-nitro-benzenesulfinyl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of N-[3-(3-formyl-4-nitro-phenylsulfanyl)-phenyl]-benzenesulfonamide (0.0034 mol) and 3-Chloro-benzenecarboperoxoic acid (also known as MCPBA or meta-chloroperbenzoic acid) (0.7 g; 75%) in CHCl3 (q.s.) was stirred for 4 hours at room temperature. Then a NaHCO3 solution was added, and the reaction mixture was stirred. The organic layer was separated, dried, and filtered, and the solvent was evaporated. The residue was purified by column chromatography over Biotage (gradient eluent: CH2Cl2:CH3OH). The purest product fractions were collected, and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. stirringthe reaction mixture was stirred
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography over Biotage (gradient eluent: CH2Cl2:CH3OH)
  7. customThe purest product fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b94f8f251a6346b59f0fccc1853d5f0a
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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