N-Acetylsulfanilyl chloride → 4-Acetamidobenzenesulfonyl azide

HRID 1480573Notes

Reaction equation

HRID 1480573 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-e110f93bd0044c208f69b51944bb41b4
Source dataset
uspto-grants-2016_08
Patent number
US09409886B2

Reaction notes

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