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

HRID 1679397Notes

Reaction equation

HRID 1679397 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[N+:12]([CH:15]=[C:16](SC)[S:17][CH3:18])([O-:14])=[O:13]>C(O)C>[N+:12]([CH:15]=[C:16]([S:17][CH3:18])[NH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)([O-:14])=[O:13]

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]ethyleneYield 29.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[(2-aminoethyl)thiomethyl]pyridine (5.0 g) and 1-nitro-2,2-bis-methylthioethylene (5.28 g) in ethanol was heated under reflux for 3 hours. Concentration and chromatographic purification of the product on a column of silica gel with elution by iso-propyl alcohol-ethylacetate (1:5) gave 1-nitro-2-methylthio-2-[2-(2-pyridylmethylthio)ethylamino]ethylene (2.49 g), m.p. 95.5°-96.5°.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationConcentration and chromatographic purification of the product on a column of silica gel
  3. washwith elution by iso-propyl alcohol-ethylacetate (1:5)

Sources & evidence

ORD record
ord-85f050ae405b45438f5f4c800c35707d
Source dataset
uspto-grants-1978_03
Patent number
US04080459

Reaction notes

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