m-Chloroperbenzoic acid → 2-nitro-N-(2-(oxiran-2-yl)ethyl)-N-phenylbenzenesulfonamide

HRID 332092Notes

Reaction equation

HRID 332092 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([N:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27])(=[O:19])=[O:18])[CH2:13][CH:14]=[CH2:15]>C(Cl)(Cl)Cl.O.C([O-])(O)=O.[Na+]>[N+:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[S:17]([N:16]([CH2:12][CH2:13][CH:14]1[CH2:15][O:9]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:19])=[O:18])([O-:28])=[O:27]

Participants

6

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 44131079N-(but-3-enyl)-2-nitro-N-phenylbenzenesulfonamide

Product 1

HCID 580971922-nitro-N-(2-(oxiran-2-yl)ethyl)-N-phenylbenzenesulfonamideYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

mCPBA (77%, 0.0550 g, 0.246 mmol) was added to N-(but-3-enyl)-2-nitro-N-phenylbenzenesulfonamide (0.0653 g, 0.196 mmol) in 1 mL CHCl3 at 0° C. The mixture was stirred at 0° C. for 30 min, then gradually warmed up to room temperature and continued to stir for 18 hr. After TLC showed the disappearance of starting material, the reaction mixture was diluted with a 1:1 mixture of water and saturated NaHCO3 (2×10 mL) and water (10 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using Hexanes/EtOAc to afford 0.0662 g colorless oil as product, yield 96.9%.

Workup

  1. temperaturegradually warmed up to room temperature
  2. stirringto stir for 18 hr
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customevaporated
  5. customto afford the crude product, which

Sources & evidence

ORD record
ord-7d02e7dba75d46c8b676a7f7ca27c7d2
Source dataset
uspto-grants-2014_11
Patent number
US08877797B2

Reaction notes

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