Water → HCID 178502623, compound

HRID 1018128Notes

Reaction equation

HRID 1018128 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[N:10][OH:11])[C:2]1=[N:12][OH:13].[H-].[Na+].S(OC)(O[CH3:20])(=O)=O.O>CN(C)C=O>[CH3:20][O:11][N:10]=[C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][C:2]1=[N:12][OH:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 178526330HCID 178526330, compound

Product 1

HCID 178502623HCID 178502623, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 11 g (0.0617 mol) of benzofuran-2,3-dione dioxime in 50 ml of dimethylformamide is added dropwise to a suspension of 2.4 g (0.06 mol) of 60% strength sodium hydride in 25 ml of dimethylformamide, and stirring is effected at 20° C. for one hour. 7.55 g (0.06 mol) of dimethyl sulphate are then added dropwise and stirring is continued at 20° C. for a further 16 hours. The reaction mixture is poured into water and the resulting mixture is extracted with ethyl acetate, the organic phase is dried over sodium sulphate and concentrated under reduced pressure. The residue is chromatographed over silica gel using hexane/acetone (7:3). Stirring the residue with diethyl ether affords 0.7 g of benzofuran-2,3-dione3-(O-methyl-oxime)2-oxime (VIII-1) as a mixture of stereoisomers consisting of 90.6% of isomer A and 9% of isomer B (HPLC).

Workup

  1. stirringstirring
  2. waitis continued at 20° C. for a further 16 hours
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed over silica gel
  7. stirringStirring the residue with diethyl ether

Sources & evidence

ORD record
ord-65d94984e97e4e65be057f7aedc9b17f
Source dataset
uspto-grants-2002_11
Patent number
US06479675B1

Reaction notes

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