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

HRID 404287Notes

Reaction equation

HRID 404287 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-ea8a6a5ef39141ab8782760242eef892
Source dataset
uspto-grants-2014_06
Patent number
US08748473B2

Reaction notes

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