HCID 136378422, compound → HCID 18957950, compound

HRID 2379094Notes

Reaction equation

HRID 2379094 reaction equation
[CH3:1][N:2]1[CH2:6][C:5](=[N:7][OH:8])[C:4](=[N:9][OH:10])[C:3]1=[O:11]>O.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[Fe+3]>[CH3:1][N:2]1[C:3](=[O:11])[C:4]2[C:5](=[N+:7]([O-:8])[O:10][N:9]=2)[CH2:6]1

Participants

6

Reactant 1

HCID 136378422HCID 136378422, compound

Product 1

HCID 18957950HCID 18957950, compoundYield 34.2%

Reagents, catalysts & solvents 4

HCID 26250Potassium ferricyanideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 13.0 g (38 mmol) of potassium hexacyanoferrate(III) in 40 ml of water and 3 ml of saturated sodium carbonate solution is added dropwise to a suspension of 1.0 g (6.4 mmol) of 1-methyl-2,3,4-pyrrolidinetrione-3,4-dioxime in 50 ml of ethyl acetate, and the mixture is stirred at room temperature for 2 hours. The organic phase is separated off and concentrated, and the residue is purified by flash chromatography (ethyl acetate/cyclohexane 60:40). 0.34 g (34%) of 5,6-dihydro-5-methyl-4H-pyrrolo[3,4-c][1,2,5]oxadiazole-4-one-1-oxide and -3-oxide is obtained in the ratio 1:2 (NMR), m.p. 49°-52° C.

Workup

  1. customThe organic phase is separated off
  2. concentrationconcentrated
  3. customthe residue is purified by flash chromatography (ethyl acetate/cyclohexane 60:40)

Sources & evidence

ORD record
ord-2419dc6a66174f46a9d508e92c24ea33
Source dataset
uspto-grants-1994_11
Patent number
US05360812

Reaction notes

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