Propane sultone → 3-Azidopropane-1-sulfonic acid

HRID 404998Notes

Reaction equation

HRID 404998 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]1[CH2:11][S:8](=[O:10])(=[O:9])[O:7][CH2:6]1>O.CC(C)=O>[N:1]([CH2:6][CH2:5][CH2:11][S:8]([OH:10])(=[O:9])=[O:7])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 14264Propane sultoneHCID 33557Sodium Azide

Product 1

HCID 589318663-Azidopropane-1-sulfonic acidYield 92%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of sodium azide (3.5 g, 50 mmol) in water (25 mL) was added a solution of 1,3-propane sultone (6.1 g, 50 mmol) in acetone (25 mL). The reaction mixture was stirred at room temperature for 24 h then concentrated to dryness. The resulting solid was suspended in diethyl ether (100 mL) and stirred at reflux for 1 h. The suspension was cooled to room temperature and the solid was collected by filtration, washed with acetone and diethyl ether, and dried under vacuum, affording of 3-azido-1-propanesulfonic acid (7.6 g, 80%).

Workup

  1. concentrationthen concentrated to dryness
  2. stirringstirred
  3. temperatureat reflux for 1 h
  4. temperatureThe suspension was cooled to room temperature
  5. filtrationthe solid was collected by filtration
  6. washwashed with acetone and diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6da3230e60b741dcabccb75ce3d4670e
Source dataset
uspto-grants-2014_06
Patent number
US08748656B2

Reaction notes

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