Triethylamine → O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

HRID 1290626Notes

Reaction equation

HRID 1290626 reaction equation
CC1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10](Cl)(=[O:12])=[O:11].C(OC(=O)[NH:20][OH:21])(C)(C)C.C(N([CH2:28][CH3:29])CC)C>C(OCC)C>[NH2:20][O:21][S:10]([C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:28]=1[CH3:29])(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineYield 58.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 25.0 grams (114 mmole) of 2,4,6-trimethyl-benzenesulfonyl chloride, 15.2 grams (114 mmole) of t-butyl-N-hydroxy-carbamate, and 350 mL of diethyl ether, cooled in an ice bath, was added dropwise 11.4 grams (114 mmole) of triethylamine. Upon completion of the addition the reaction mixture was stirred at ambient temperature for about 18 hours, then filtered, and the filtrate was concentrated under reduced pressure. The concentrate was taken up in toluene and petroleum ether, filtered, and 150 mL of trifluoroacetic acid was added. The reaction mixture was stirred for 1.5 hours in an ice bath, then poured into ice-water, filtered, and extracted with diethyl ether. The organic extract was dried with magnesium sulfate and filtered. Petroleum ether was added to the filtrate, and the resulting precipitate 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. additionUpon completion of the addition the reaction mixture
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. filtrationpetroleum ether, filtered
  5. addition150 mL of trifluoroacetic acid was added
  6. stirringThe reaction mixture was stirred for 1.5 hours in an ice bath
  7. additionpoured into ice-water
  8. filtrationfiltered
  9. extractionextracted with diethyl ether
  10. extractionThe organic extract
  11. dry with materialwas dried with magnesium sulfate
  12. filtrationfiltered
  13. additionPetroleum ether was added to the filtrate
  14. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-000f6519000646b9b0b166abe7e7b3fe
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

Loading…