Peracetic Acid → HCID 14274524, compound

HRID 330460Notes

Reaction equation

HRID 330460 reaction equation
[O:1](N=[N+]=[N-])S(N=[N+]=[N-])(=O)=O.[CH2:11]([O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:25]=[N+:26]=[N-:27])(=[O:24])=[O:23])=[CH:18][CH:17]=1)[C:12](=[CH2:14])[CH3:13].C(OO)(=O)C.C([O-])(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[N:25]([S:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:11][C:12]2([CH3:13])[O:1][CH2:14]2)=[CH:21][CH:20]=1)(=[O:23])=[O:24])=[N+:26]=[N-:27]

Participants

7

Reactant 4

HCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 14274523HCID 14274523, compoundHCID 18945546HCID 18945546, compound

Product 1

HCID 14274524HCID 14274524, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
41 °C

Procedure

To show another example of the epoxy-sulfonylazide of the instant invention, a solution of p-methallyloxybenzenesulfonylazide (506 parts) in methylene chloride (1,450) parts is stirred and heated to reflux (41° C.) then a solution of 35% peracetic acid in acetic acid (521.5 parts) containing sodium acetate (15.6 parts) is added slowly from an addition funnel over 15 minutes. An additional 40 parts of methylene chloride is added to adjust the reflux temperature to 45° C. After 6 hrs stirring and refluxing at 45° C. the reaction is quenched with 835 parts of distilled water. The layers are separated and the organic phase is washed with 555 parts of 10% sodium sulfite, 835 parts of sodium bicarbonate, and 565 parts of distilled water containing 23 parts of trioctylammonium chloride. The solution is dried azeotropically, and the solvent is removed at 55° C. and 20 mm to yield 528 parts of 3-(p-azidosulfonylphenoxy)-2-methylpropylene oxide as a white, crystalline solid. This represents a yield of 98%.

Workup

  1. temperatureheated
  2. additionis added slowly from an addition funnel over 15 minutes
  3. customto 45° C
  4. temperaturerefluxing at 45° C. the reaction
  5. customis quenched with 835 parts of distilled water
  6. customThe layers are separated
  7. washthe organic phase is washed with 555 parts of 10% sodium sulfite, 835 parts of sodium bicarbonate, and 565 parts of distilled water containing 23 parts of trioctylammonium chloride
  8. customThe solution is dried azeotropically
  9. customthe solvent is removed at 55° C.

Sources & evidence

ORD record
ord-79384cb9f8e24d9bb1648c2bb5324b77
Source dataset
uspto-grants-1990_01
Patent number
US04897144

Reaction notes

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