Acetic Acid → 3'-Chloro-4'-((methylsulfonyl)amino)acetophenone

HRID 466352Notes

Reaction equation

HRID 466352 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Cl:15][O-].[Ca+2].Cl[O-].C(O)(=O)C>O>[Cl:15][C:8]1[CH:9]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=[CH:6][C:7]=1[NH:10][S:11]([CH3:14])(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24504Calcium hypochlorite2×HCID 684083N-(4-acetylphenyl)methanesulfonamide

Product 1

HCID 198734583'-Chloro-4'-((methylsulfonyl)amino)acetophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2.13 g (10 mmole) of N-(4-acetylphenyl)methanesulfonamide in 50 ml of alcohol and 50 ml of water at 30° C. is added 1.43 g (10 mmol) of calcium hypochlorite. The solution is stirred for 24 hrs and an additional 1.43 g of calcium hypochlorite added. The mixture is stirred for 3 days at room temperature. The mixture is acidified with acetic acid to pH 6; concentrated and extracted into water-methylene chloride. The organic layer is dried, evaporated and the residue flash chromatographed on silica gel eluting in succession with 25% and 50% ethyl acetate-pet. ether. The solid product is recrystallized from Et2O-pet. ether; m.p. 129°-131° C. MW 247.71.

Workup

  1. stirringThe mixture is stirred for 3 days at room temperature
  2. concentrationconcentrated
  3. extractionextracted into water-methylene chloride
  4. customThe organic layer is dried
  5. customevaporated
  6. customthe residue flash chromatographed on silica gel eluting in succession with 25% and 50% ethyl acetate-pet. ether
  7. customThe solid product is recrystallized from Et2O-pet. ether

Sources & evidence

ORD record
ord-5a8495b24b8a4b4b991998f777e295bb
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

Loading…