Perchloric Acid → O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

HRID 1621168Notes

Reaction equation

HRID 1621168 reaction equation
[C:1]1([CH3:19])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12]/[N:13]=C(\OCC)/C)(=[O:11])=[O:10].Cl(O)(=O)(=O)=O>C1COCC1>[C:1]1([CH3:19])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH2:13])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 5748625ethyl (1E)-N-{[(2,4,6-trimethylphenyl)sulfonyl]oxy}ethanimidate

Product 1

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under argon atmosphere, (Z)-ethyl N-mesitylsulfonyloxyacetimidate (15 g, 52.6 mmol) was dissolved in THF (13 mL) at 0° C. Perchloric acid (70% aqueous solution, 22.6 g, 13.6 mL, 158 mmol) was then added dropwise at 0-5° C. over a period of 50 min. After 10 min, precipitation started and THF (3 mL) was added. After stirring at 0° C. for 30 min, the mixture was poured into ice water (200 mL) under vigorous stirring giving a white suspension. After additional stirring for 15 min, the suspension was filtered and the precipitate was washed with ice water. The white solid was dissolved in diethyl ether (150 mL), dried over MgSO4 and evaporated at RT without heating while the flask was cooled (very important, because the compound can decompose at 25° C.!) to give O-(mesitylsulfonyl)hydroxylamine as white solid (9.2 g, 42.7 mmol, 81.3%). The crude product was used further without purification since O-(mesitylsulfonyl)hydroxylamine is unstable at 25° C.!

Workup

  1. customprecipitation
  2. additionTHF (3 mL) was added
  3. additionthe mixture was poured into ice water (200 mL)
  4. stirringunder vigorous stirring
  5. customgiving a white suspension
  6. stirringAfter additional stirring for 15 min
  7. filtrationthe suspension was filtered
  8. washthe precipitate was washed with ice water
  9. dissolutionThe white solid was dissolved in diethyl ether (150 mL)
  10. dry with materialdried over MgSO4
  11. customevaporated at RT
  12. temperaturewithout heating while the flask
  13. temperaturewas cooled (very important, because the compound
  14. customcan decompose at 25° C.

Sources & evidence

ORD record
ord-f14cd24aa4484c8c8a629e96fd3b0fd4
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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