Triethylamine → Di-(methanesulfonyl)-dimethylglyoxime

HRID 261130Notes

Reaction equation

HRID 261130 reaction equation
[CH3:1][C:2](=[N:7][OH:8])[C:3]([CH3:6])=[N:4][OH:5].[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(N(CC)CC)C>O1CCOCC1>[CH3:9][S:10]([O:5][N:4]=[C:3]([CH3:6])[C:2]([CH3:1])=[N:7][O:8][S:10]([CH3:9])(=[O:12])=[O:11])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 135459645Dimethylglyoxime

Product 1

HCID 54292485Di-(methanesulfonyl)-dimethylglyoximeYield 77.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 300 ml of 1,4 dioxane in a round-bottom flask was added 11.6 g (0.1 mole) of dimethylglyoxime. When the solid had completely dissolved, 22.9 g (0.2 mole) of methanesulfonyl chloride was added. The mixture was stirred and 20.2 g (0.2 mole) triethylamine was added dropwise. The reaction mixture was stirred for 51/2 hours during which time a precipitate was formed. The dioxane was removed by evaporation under reduced pressure. The residue was stirred in ice water, then filtered. The solid product was dissolved in dichloromethane and dried over anhydrous sodium sulfate. The slurry was filtered and the solvent was removed in a rotary evaporator. The solid residue was stirred in cold ethanol, then filtered and dried in a vacuum oven, giving 21.05 g (77% yield) of di-(methanesulfonyl)-dimethylglyoxime with mp 169-172° C.

Workup

  1. dissolutionWhen the solid had completely dissolved
  2. stirringThe reaction mixture was stirred for 51/2 hours during which time a precipitate
  3. customwas formed
  4. customThe dioxane was removed by evaporation under reduced pressure
  5. stirringThe residue was stirred in ice water
  6. filtrationfiltered
  7. dissolutionThe solid product was dissolved in dichloromethane
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationThe slurry was filtered
  10. customthe solvent was removed in a rotary evaporator
  11. stirringThe solid residue was stirred in cold ethanol
  12. filtrationfiltered
  13. customdried in a vacuum oven

Sources & evidence

ORD record
ord-88dc395a2f9c4015af6f01cd75a420d5
Source dataset
uspto-grants-1979_08
Patent number
US04164395

Reaction notes

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