Hydrogen Peroxide → 1-Nitro2-methylthio-2-methylsulphinylethylene

HRID 436849Notes

Reaction equation

HRID 436849 reaction equation
[CH3:1][S:2][C:3]([S:8][CH3:9])=[CH:4][N+:5]([O-:7])=[O:6].[OH:10]O>C(O)(=O)C.CC(CC)=O>[CH3:1][S:2]([C:3]([S:8][CH3:9])=[CH:4][N+:5]([O-:7])=[O:6])=[O:10]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 544870941-Nitro2-methylthio-2-methylsulphinylethylene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a stirred solution in acetic acid (4,500 ml) of 1,1-bismethylthio-2-nitroethylene (165 g) at 60° was added over 15 minutes 30% (100 volume) hydrogen peroxide (113 ml) and the reaction mixture maintained, with stirring, at 60° for 17 hours. Evaporation of the solvent under reduced pressure gave a residue which was taken up in methylethylketone, reevaporated and finally crystallised from methylethylketone to yield the title product as a yellow solid m.p. 137°-143°. Further purification yielded the pure "Z" and "E" isomers. One of these had m.p. 145°-148° and from the mother liquors the other isomer was obtained after further working up and recrystallisation from methylal, m.p. 90°-93°.

Workup

  1. temperaturethe reaction mixture maintained
  2. customEvaporation of the solvent under reduced pressure
  3. customgave a residue which
  4. customreevaporated
  5. customfinally crystallised from methylethylketone

Sources & evidence

ORD record
ord-96594ec059a94ef7bd34cdd1dfd5625f
Source dataset
uspto-grants-1977_06
Patent number
US04028379

Reaction notes

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