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

HRID 1749497Notes

Reaction equation

HRID 1749497 reaction equation
[CH2:1]([NH:9][C:10](=[O:12])[CH3:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[S:13]([Cl:17])(=O)(=[O:15])[OH:14]>>[C:10]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:13]([Cl:17])(=[O:15])=[O:14])=[CH:5][CH:4]=1)(=[O:12])[CH3:11]

Participants

3

Reactant 2

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

Product 1

HCID 3015782p-(2-Acetamidoethyl)benzenesulphonyl chlorideYield 45%

Procedure

N-Phenethylacetamide (4.50 g, 27.6 mmol) was added to sulfurochloridic acid (30 mL) slowly at 0-5° C. The resulting reaction mixture was stirred at room temperature for 2 h. The reaction mixture was poured into ice-water and stirred for 10 min. The mixture was extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to afford the title compound as a brown solid (3.30 g, 12.64 mmol, 45% yield). MS (ESI) m/z 262.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred for 10 min
  3. extractionThe mixture was extracted with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3f24ffb28f2141bbb946d7b287d56a41
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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