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

HRID 62157
Notes
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Reaction equation

HRID 62157 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6212ChloroformSolvent
HCID 516892
Sodium Bicarbonate
Solvent

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-6285f67a982b476b9e700d3806c5b70e
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09446022B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes