Potassium Carbonate → 2-(Oxiran-2-yl)benzene-1-sulfonamide

HRID 1607789Notes

Reaction equation

HRID 1607789 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10])=[CH2:2].C(=O)([O-])[O-:14].[K+].[K+]>C(Cl)(Cl)Cl>[O:14]1[CH2:2][CH:1]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH2:12])(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 113674032-Ethenylbenzenesulfonamide

Product 1

HCID 138845232-(Oxiran-2-yl)benzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution consisting of 2-ethenylbenzenesulfonamide (1.5 g, 8.1 mmol) m-chloroperbenzoic acid (1.4 g, 8.1 mmol) and potassium carbonate (1.1 g, 8.1 mmol) in 150 ml of chloroform was stirred for 4 days at room temperature. The reaction was filtered and the filtrate was washed with saturated sodium bicarbonate. The organic layer was separated, dried and concentrated. The resulting oil was flash chromatographed (methylene chloride) to yield the subject compound as a white solid. m.p. 136°-139° C.

Workup

  1. filtrationThe reaction was filtered
  2. washthe filtrate was washed with saturated sodium bicarbonate
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed (methylene chloride)

Sources & evidence

ORD record
ord-589e1cb3c2544f2c8cbc5de97132190a
Source dataset
uspto-grants-1989_09
Patent number
US04867783

Reaction notes

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