Chlorosulfonic acid → p-(2-Acetamidoethyl)benzenesulphonyl chloride

HRID 2266394Notes

Reaction equation

HRID 2266394 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([NH:14][C:15](=[O:17])[CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl>[C:15]([NH:14][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:10][CH:9]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 70143N-(2-phenylethyl)acetamide

Product 1

HCID 3015782p-(2-Acetamidoethyl)benzenesulphonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30.6 ml chlorosulfonic acid were added in one portion to 25.0 g N-phenethyl-acetamide. The reaction mixture was stirred at room temperature for one hour, then 100 ml dichloromethane were added and the reaction mixture was poured on ice water. The organic layer was separated washed twice with 50 ml brine and then dried over MgSO4. The solvent was removed in vacuo to obtain 22.0 g 4-(2-Acetylamino-ethyl)-benzenesulfonyl chloride as a white solid.

Workup

  1. additionthe reaction mixture was poured on ice water
  2. customThe organic layer was separated
  3. washwashed twice with 50 ml brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6cbc2ff5fa174d6185f6771accdfec30
Source dataset
uspto-grants-2010_12
Patent number
US07858647B2

Reaction notes

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