N-Acetylsulfanilyl chloride → 4-Acetamidobenzenesulfonyl azide

HRID 1112035Notes

Reaction equation

HRID 1112035 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N-:15]=[N+:16]=[N-:17].[Na+]>CC(C)=O.O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:15]=[N+:16]=[N-:17])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 33557Sodium Azide

Product 1

HCID 51291854-Acetamidobenzenesulfonyl azideYield 80%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

23.4 g (0.1 mole) of p-acetamidobenzenesulfonyl chloride was dissolved in 300 ml of acetone; any solid impurities present were removed by gravity filtration. The acetone solution was added to a one liter Erlenmeyer flask and stirring maintained magnetically. To this solution was added 8.5 g (.13 mole) of sodium azide dissolved in a minimum amount of water. The reaction mixture develops a red-brown color and a solid material was formed over 30 minute reaction time. The resulting slurry was poured into 1.5 l of ice water and solids removed by filtration. The product was crystallized from benzene to give 18.8 g (80% yield).

Workup

  1. customany solid impurities present were removed by gravity filtration
  2. additionThe acetone solution was added to a one liter Erlenmeyer flask
  3. temperaturemaintained magnetically
  4. customa solid material was formed over 30 minute
  5. customreaction time
  6. customremoved by filtration
  7. customThe product was crystallized from benzene
  8. customto give 18.8 g (80% yield)

Sources & evidence

ORD record
ord-f95ef0d810864d8aa3d3ac58c253fa61
Source dataset
uspto-grants-1978_10
Patent number
US04120652

Reaction notes

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