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

HRID 219426Notes

Reaction equation

HRID 219426 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>O1CCOCC1>[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 2724212Ethyl N-[[(2,4,6-trimethylphenyl)sulfonyl]oxy]ethanimidate

Product 1

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl N-mesitylsulfonyloxyacetimidate (20 g, 65.7 mmol, 1 eq) was dissolved in 1,4-dioxane (6 ml) and the solution was cooled to 0° C. To the mixture was added dropwise Perchloric acid (10 in), and the reaction mixture was then stirred at 0° C. for 45 minutes. The solution was poured into ice water, and the solid precipitated was filtered and washed with water and dried for 15 minutes in vacuum. The sample was stored in plastic container at −20° C. 1HNMR (400 MHz, DMSO-d6): δ 2.32 (s, 3H), 2.64 (s, 6H), 4.98 (br peak, 2H), 6.99 (s, 2H).

Workup

  1. customthe solid precipitated
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried for 15 minutes in vacuum
  5. customwas stored in plastic container at −20° C

Sources & evidence

ORD record
ord-813830b4fdd24f8387fce3c308e9efc2
Source dataset
uspto-grants-2012_06
Patent number
US08198449B2

Reaction notes

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