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

HRID 705364Notes

Reaction equation

HRID 705364 reaction equation
[C:1]1([CH3:21])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH:13]C(=O)OC(C)(C)C)(=[O:11])=[O:10].FC(F)(F)C(O)=O>O>[C:1]1([CH3:21])[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 6422Trifluoroacetic acidHCID 3592851,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl mesitylsulfonyloxycarbamate (1.51 g, 5.42 mmol) was added to cold (0° C.) trifluoroacetic acid (10.8 mL) and the mixture was stirred at 0° C. for 45 minutes. The mixture was diluted with cold (0° C.) water and the white precipitate was collected by filtration and washed with 1000 mL of cold (0° C.) water. The solid was dried by suction for about 5 minutes and then dissolved in cold (0° C.) dichloromethane and dried (Na2SO4). The solution was filtered and the filtrate was concentrated to a volume of about 12 mL on the rotary evaporator without heating. The solution was then directly used in the next step.

Workup

  1. filtrationthe white precipitate was collected by filtration
  2. washwashed with 1000 mL of cold (0° C.) water
  3. customThe solid was dried by suction for about 5 minutes
  4. dissolutiondissolved in cold (0° C.) dichloromethane
  5. dry with materialdried (Na2SO4)
  6. filtrationThe solution was filtered
  7. concentrationthe filtrate was concentrated to a volume of about 12 mL on the rotary evaporator
  8. temperaturewithout heating

Sources & evidence

ORD record
ord-a9232f0a74524116b766985a1d21d841
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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