Trifluoroacetic acid → O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

HRID 440704Notes

Reaction equation

HRID 440704 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[S:17]([O:20][NH:21]C(=O)OC(C)(C)C)(=[O:19])=[O:18]>>[NH2:21][O:20][S:17]([C:10]1[C:11]([CH3:16])=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=1[CH3:8])(=[O:18])=[O:19]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 3592851,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate

Product 1

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineYield 0.1%

Procedure

Trifluoroacetic acid, 80.0 mL, was stirred and cooled in an ice-water bath, and 25.0 grams (0,079 mole) of 1,1-dimethylethyl N-(2,4,6-trimethylphenylsulfonyloxy)carbamate was added portionwise. Upon completion of the addition, the reaction mixture was stirred for 90 minutes, then poured into ice-water The resultant solid was collected by filtration and dissolved in diethyl ether. The solution was then dried with magnesium sulfate and filtered. The solid product was precipitated from the filtrate by the addition of petroleum ether. The solid was collected by filtration, yielding 14.4 grams of 1-aminooxysulfonyl-2,4,6-trimethylbenzene. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturecooled in an ice-water bath
  2. additionUpon completion of the addition
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in diethyl ether
  5. dry with materialThe solution was then dried with magnesium sulfate
  6. filtrationfiltered
  7. customThe solid product was precipitated from the filtrate by the addition of petroleum ether
  8. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-1a7954263c39476bb49742ebb194580a
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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