Benzanilide → 4-Benzamidobenzene-1-sulfonyl chloride

HRID 1764053Notes

Reaction equation

HRID 1764053 reaction equation
[C:1]([NH:9][C:10]1[CH:19]=[CH:18][C:13]([S:14](F)(=[O:16])=[O:15])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC1C=CC=CC=1)(=O)C1C=CC=CC=1.[Cl:35]S(O)(=O)=O>>[C:1]([NH:9][C:10]1[CH:19]=[CH:18][C:13]([S:14]([Cl:35])(=[O:16])=[O:15])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7168BenzanilideHCID 24638Chlorosulfonic acidHCID 22769907HCID 22769907, compound

Product 1

HCID 133153384-Benzamidobenzene-1-sulfonyl chlorideYield 41%

Conditions

Temperature
60 °C

Procedure

N-benzoylsulfanilyl chloride was prepared as starting material for N-benzoylsulfanilyl fluoride in the following manner: A 15 gm (0.076 mole) portion of benzanilide was added with stirring to 26 ml (0.38 mole) of chlorosulfonic acid at 0° C. The mixture was then allowed to stir at 60° C for two hours, then cooled to room temperature and poured into ca 200 gm of ice. The sulfonyl chloride was recovered by filtration and recrystallized from chlorobenzene, giving 9.1 gm (41% yield) with mp 176°-178° C. The assigned structure was in agreement with the chemical analysis and the NMR and IR spectra.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe sulfonyl chloride was recovered by filtration
  3. customrecrystallized from chlorobenzene
  4. customgiving 9.1 gm (41% yield) with mp 176°-178° C

Sources & evidence

ORD record
ord-3a3cb289f3e240b5a171fc9d37425d95
Source dataset
uspto-grants-1978_09
Patent number
US04115059

Reaction notes

Loading…