Potassium Iodide → HCID 178475863, compound

HRID 1729979Notes

Reaction equation

HRID 1729979 reaction equation
[C:1]([C:4]1[C:13]([CH2:14]Br)=[N+:12]([O-:16])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]=1[O-:17])(=[O:3])[CH3:2].[C:18]([O-:21])(=[O:20])[CH3:19].[K+].[I-].[K+]>CN(C)C=O>[C:1]([C:4]1[C:13]([CH2:14][O:21][C:18](=[O:20])[CH3:19])=[N+:12]([O-:16])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]=1[O-:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 517044Potassium AcetateHCID 178465859HCID 178465859, compound

Product 1

HCID 178475863HCID 178475863, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred slurry of 50.0 g. (0.168 mol.) of 2-acetyl-3-bromomethylquinoxaline 1,4 dioxide in 200 ml. of N,N-dimethylformamide, was added 18.2 g. (0.185 mol.) of potassium acetate, followed by 4.15 g. (0.025 mol.) of finely ground potassium iodide. Stirring was continued for 20 minutes at ambient temperature, and then the reaction mixture was filtered. The dark filtrate was added dropwise to 4,000 ml. of ether, and the solid which precipitated was removed by filtration and discarded. Evaporation of the ether in vacuo afforded a yellow solid which was recrystallized from methanol. This gave 31.6 g. (76% yield) of 2-acetyl-3-acetoxymethylquinoxaline 1,4-dioxide having m.p. 124°-125° C.

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionThe dark filtrate was added dropwise to 4,000 ml
  3. customof ether, and the solid which precipitated
  4. customwas removed by filtration
  5. customEvaporation of the ether in vacuo
  6. customafforded a yellow solid which
  7. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-27e923d124984d56820c0422beea5bb4
Source dataset
uspto-grants-1976_11
Patent number
US03991053

Reaction notes

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