Acetanilide → N-Acetylsulfanilyl chloride

HRID 1787983Notes

Reaction equation

HRID 1787983 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[CH3:7]>>[C:6]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:12][CH:11]=1)(=[O:8])[CH3:7]

Participants

3

Reactant 2

HCID 904AcetanilideHCID 24638Chlorosulfonic acid

Product 1

HCID 8481N-Acetylsulfanilyl chlorideYield 48.3%

Conditions

Temperature
100 °C

Procedure

Chlorosulfonic acid (10 ml, 0.15 mol) is added dropwise slowly to acetanilide (4 g, 0.029 mol). The mixture is then heated to 100° C. for one hour. The oil that forms is cooled and carefully poured onto ice. The resulting precipitate is collected by filtration affording the desired product (3.4 g, 0.014 mol, 48% yield). The sulfonyl chloride is used directly without further purification.

Workup

  1. temperatureThe oil that forms is cooled
  2. additioncarefully poured onto ice
  3. filtrationThe resulting precipitate is collected by filtration

Sources & evidence

ORD record
ord-97bda1e20a6f41ceba71300b911c2899
Source dataset
uspto-grants-2009_03
Patent number
US07511133B2

Reaction notes

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