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

HRID 2258632Notes

Reaction equation

HRID 2258632 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 84.7%

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 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 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-85b8d4b348a74a14bd9f83f09cc67c47
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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