Dimethylamine → 1-Dimethylamino-1-methylthio-2-nitroethylene

HRID 1492046Notes

Reaction equation

HRID 1492046 reaction equation
[N+:1]([CH2:4][C:5]([S-:7])=S)([O-:3])=[O:2].[K+].[K+].[N+]([CH2:13]C([S-])=S)([O-])=O.[CH3:17][NH:18][CH3:19].S(OC)(OC)(=O)=O>O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[CH3:17][N:18]([CH3:19])[C:5]([S:7][CH3:13])=[CH:4][N+:1]([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 6497Dimethyl SulfateHCID 18954385HCID 18954385, compound

Product 1

HCID 538966631-Dimethylamino-1-methylthio-2-nitroethylene

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent2×

Procedure

To a solution of dipotassium nitrodithioacetate (118 g) dissolved in water (630 ml), dimethylamine (1.1 equivalents) was added as a 40% w/w solution in water. After stirring for 6 hours at 20°-25° C., benzyltrimethylammonium chloride (7 g ) was charged followed by dimethyl sulphate (175 g ) over one hour. After stirring overnight, the reaction mixture was extracted three times with 100 ml aliquots of dichloromethane. After drying over MgSO4, the combined organic phases were concentrated to a red oil which was chromatographed on a silica gel column, using ethyl acetate as eluant to give, after recrystallisation from isopropanol, 36 g (40%) of the title compound, m.p. 60° C.

Workup

  1. stirringAfter stirring overnight
  2. extractionthe reaction mixture was extracted three times with 100 ml aliquots of dichloromethane
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe combined organic phases were concentrated to a red oil which
  5. customwas chromatographed on a silica gel column
  6. customto give
  7. customafter recrystallisation from isopropanol, 36 g (40%) of the title compound, m.p. 60° C.

Sources & evidence

ORD record
ord-8eb45fa047ad482287cf55b59cac960a
Source dataset
uspto-grants-1994_12
Patent number
US05371247

Reaction notes

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