Propylene Oxide → 2-Oxiranemethanesulfonyl azide

HRID 918349Notes

Reaction equation

HRID 918349 reaction equation
[CH2:1]([S:4]([N:7]=[N+:8]=[N-:9])(=[O:6])=[O:5])[CH:2]=[CH2:3].C([O-])(=[O:12])C.[Na+].C(OO)(=O)C.C=CC.O1C(C)C1>O.C(Cl)Cl.C(O)(=O)C>[O:12]1[CH2:3][CH:2]1[CH2:1][S:4]([N:7]=[N+:8]=[N-:9])(=[O:6])=[O:5]

Participants

9

Reactant 5

HCID 6378Propylene OxideHCID 6585Peracetic Acid2×HCID 8252PropyleneHCID 517045Sodium AcetateHCID 20300589HCID 20300589, compound

Product 1

HCID 203005412-Oxiranemethanesulfonyl azide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 14.7 parts of 2-propene-1-sulfonyl azide in 105 parts of glacial acetic acid containing one part of sodium acetate was added with stirring at room temperature 40% peracetic acid in an amount in excess of that required to convert the propene radical to an epoxypropane radical. The reaction was stirred at room temperature until the peracetic acid content remained constant and then diluted with 200 parts of water and 135 parts of methylene chloride. The methylene chloride layer was removed and washed with water 5 times and then dried over magnesium sulfate. The methylene chloride solvent was removed leaving 15.1 parts of 2,3-epoxypropane-1-sulfonyl azide. The results of an infrared analysis of the product for % azido nitrogen and oxirane oxygen is tabulated below:

Workup

  1. customThe methylene chloride layer was removed
  2. washwashed with water 5 times
  3. dry with materialdried over magnesium sulfate
  4. customThe methylene chloride solvent was removed

Sources & evidence

ORD record
ord-cfba56fb02aa4e5182d023a8c5193de3
Source dataset
uspto-grants-1976_07
Patent number
US03971627

Reaction notes

Loading…