2-Naphthalenesulfonyl chloride → 2-Naphthalenesulfonyl azide

HRID 1602995Notes

Reaction equation

HRID 1602995 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[S:15](Cl)(=[O:17])=[O:16]>O.CC(C)=O>[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[S:15]([N:1]=[N+:2]=[N-:3])(=[O:16])=[O:17]

Participants

5

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 109773552-Naphthalenesulfonyl azideYield 74.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium azide (3.1 g, 44 mmol) in water (10 ml) was added dropwise at RT to a stirred solution of 2-naphthalenesulfonyl chloride (10 g, 44 mmol) in acetone (60 ml) and stirring was continued for 2 hours. Water (50 ml) was added and the resulting mixture was decanted. The surnatant was discarded, while the brown oily residue was recrystallized from light petroleum producing after drying pure title compound (7.67 g, 32.9 mmol, yield 74.7%) as white needles, m.p.=45°.

Workup

  1. customthe resulting mixture was decanted
  2. customwas recrystallized from light petroleum producing

Sources & evidence

ORD record
ord-e01af69e6fd24fa6a9f66ce7f8e68672
Source dataset
uspto-grants-1999_11
Patent number
US05985905

Reaction notes

Loading…