N-Acetylsulfanilyl chloride → 4-Acetamidobenzenesulfonyl azide

HRID 1916412Notes

Reaction equation

HRID 1916412 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1)(=[O:7])[CH3:6]>CC(C)=O.O>[C:5]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([N:1]=[N+:2]=[N-:3])(=[O:17])=[O:16])=[CH:13][CH:14]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 33557Sodium Azide2×

Product 1

HCID 51291854-Acetamidobenzenesulfonyl azideYield 87.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Sodium azide (7.8 g, 120 mmol) was charged in a 1 L round bottom flask with water. 4-Acetamidobenzene-1-sulfonyl chloride (23.4 g, 100 mmol) was dissolved in acetone, and this solution was slowly added to the solution of sodium azide. The reaction was then stirred for 16 hours at room temperature and diluted with water. The acetone was then removed. The solid was filtered to give 4-acetamidobenzenesulfonyl azide (21 g, 87%) as a white solid.

Workup

  1. customThe acetone was then removed
  2. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-c2d1e6ae66d34ba1b7ef21a562b116b5
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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