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

HRID 873310Notes

Reaction equation

HRID 873310 reaction equation
C(OC([NH:8][O:9][S:10]([C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21])(=[O:12])=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[C:14]1([CH3:21])[CH:15]=[C:16]([CH3:20])[CH:17]=[C:18]([CH3:19])[C:13]=1[S:10]([O:9][NH2:8])(=[O:12])=[O:11]

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)hydroxylamine

Conditions

Temperature
0 °C

Procedure

N-t-Butoxycarbonyl-O-(mesitylsulfonyl)hydroxylamine (4.0 g) was added to TFA (15 mL) at 0° C., and the mixture was stirred for 1 h at 0° C. The reaction mixture was poured into ice water (100 mL) and the precipitate collected by filtration. The solid was dissolved in the minimum volume of ether and precipitated by the addition of three to four times the volume of petroleum ether 40-60. The mixture was cooled to 0° C. and stirred for 15 min Filtration yielded O-(Mesitylsulfonyl)hydroxylamine (Intermediate 2) as a solid.

Workup

  1. filtrationthe precipitate collected by filtration
  2. dissolutionThe solid was dissolved in the minimum volume of ether
  3. customprecipitated by the addition of three to four times the volume of petroleum ether 40-60
  4. temperatureThe mixture was cooled to 0° C.
  5. stirringstirred for 15 min
  6. filtrationFiltration

Sources & evidence

ORD record
ord-82ba7de5d5e342a9bf6d79066b0c2a88
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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