m-Chloroperbenzoic acid → 2-Oxiranylmethoxyphenylsulfonamide

HRID 4487Notes

Reaction equation

HRID 4487 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([NH2:25])(=[O:24])=[O:23])[CH:13]=[CH2:14]>C(Cl)Cl>[O:9]1[CH2:14][CH:13]1[CH2:12][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([NH2:25])(=[O:23])=[O:24]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 133217572-[(Prop-2-en-1-yl)oxy]benzene-1-sulfonamide

Product 1

HCID 200403992-OxiranylmethoxyphenylsulfonamideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 15.3 g of 3-chloroperbenzoic acid in 270 ml of absolute methylene chloride are added 14.2 g of 2-allyloxyphenylsulfonamide over 2 minutes. The solution is then heated to reflux for 3 hours, cooled, and then washed three times with saturated sodium carbonate solution and once with water. The organic phase is dried and concentrated, affording 11.9 g of 2-oxiranylmethoxyphenylsulfonamide with a melting point of 132°-133° C.

Workup

  1. temperatureThe solution is then heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled
  4. washwashed three times with saturated sodium carbonate solution
  5. customThe organic phase is dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a8b5e717444b4d86bbebb7c007f0d53f
Source dataset
uspto-grants-1988_02
Patent number
US04726836

Reaction notes

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