4-Toluenesulfonyl chloride → Di-(p-toluenesulfonyl)dimethylglyoxime

HRID 261131Notes

Reaction equation

HRID 261131 reaction equation
[CH3:1][C:2](=[N:7][OH:8])[C:3]([CH3:6])=[N:4][OH:5].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(N([CH2:25][CH3:26])CC)C>O1CCOCC1>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([O:5][N:4]=[C:3]([CH3:6])[C:2]([CH3:1])=[N:7][O:8][S:15]([C:12]2[CH:13]=[CH:14][C:25]([CH3:26])=[CH:10][CH:11]=2)(=[O:17])=[O:16])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 135459645Dimethylglyoxime

Product 1

HCID 54479772Di-(p-toluenesulfonyl)dimethylglyoxime

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture containing 70 ml of dioxane, 2.3 g (0.02 mole) of dimethylglyoxime, 3.8 g (0.02 mole) of p-toluenesulfonyl chloride and 2.0 g (0.02 mole) of triethylamine was stirred for several days at room temperature. Dioxane was then removed by evaporation under reduced pressure and the solid residue stirred in ice water. The slurry was filtered and the solid material (4.1 g) was dried in a vacuum oven. The solid had no definite melting point.

Workup

  1. customDioxane was then removed by evaporation under reduced pressure
  2. stirringthe solid residue stirred in ice water
  3. filtrationThe slurry was filtered
  4. dry with materialthe solid material (4.1 g) was dried in a vacuum oven

Sources & evidence

ORD record
ord-52ea043bf666485fa52c635016f431ef
Source dataset
uspto-grants-1979_08
Patent number
US04164395

Reaction notes

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