1,1-Bis(methylthio)-2-nitroethylene → 1-Nitro-2-methylthio-2-[2-(2-pyridylmethylthio)ethylamino]ethylene

HRID 894124Notes

Reaction equation

HRID 894124 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[CH3:12][S:13][C:14](SC)=[CH:15][N+:16]([O-:18])=[O:17]>C(O)(C)C>[N+:16]([CH:15]=[C:14]([S:13][CH3:12])[NH:11][CH2:10][CH2:9][S:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 128894012-((2-Aminoethyl)thiomethyl)pyridine

Product 1

HCID 705703291-Nitro-2-methylthio-2-[2-(2-pyridylmethylthio)ethylamino]ethylene

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-[(2-pyridyl)methylthio]ethylamine (from the dihydrobromide, 20.0 g; 60.6 mmoles) [prepared according to the procedure described in Belgian Pat. No. 779,775] and 1,1-bis(methylthio)-2-nitroethylene [prepared according to the procedure described in Chem. Ber., 100, 591 (1967) or Acta Chem. Scand., 21, 2797 (1967)] (10.0 g; 60.6 mmoles) in isopropyl alcohol (175 ml) was stirred at ambient temperature under a positive pressure of nitrogen for 16 hours then at reflux temperature for 2 hours to complete the reaction. The mixture was cooled in an ice-water bath and the product collected by filtration. Recrystallization from isopropyl alcohol with activated carbon treatment gave 1-nitro-2-methylthio-2-{2-[(2-pyridyl)methylthio]-ethylamino}ethylene; mp 97°-99°.

Workup

  1. custom60.6 mmoles) [prepared
  2. temperatureat reflux temperature for 2 hours
  3. customthe reaction
  4. temperatureThe mixture was cooled in an ice-water bath
  5. filtrationthe product collected by filtration
  6. customRecrystallization from isopropyl alcohol with activated carbon treatment

Sources & evidence

ORD record
ord-e5db7188e7954819aa6eb7e21616b2d5
Source dataset
uspto-grants-1981_08
Patent number
US04282363

Reaction notes

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