1,1-Bis(methylthio)-2-nitroethylene → HCID 70546016, compound

HRID 444512Notes

Reaction equation

HRID 444512 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][S:7][C:8]([N+]([O-])=O)=[CH:9][NH2:10].[CH3:14][S:15][C:16](SC)=[CH:17][N+:18]([O-:20])=[O:19]>O1CCOCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][S:7][CH2:8][CH2:9][NH:10][C:16]([S:15][CH3:14])=[CH:17][N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 70547911HCID 70547911, compound

Product 1

HCID 70546016HCID 70546016, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-[(2-furanylmethyl)thio]-2-nitroethenamine (3.14 g.) and 1,1-bis-(methylthio)-2-nitroethene (13.2 g.) in dioxan (100 ml.) was heated at 100° for 11/2 hours. The solution was evaporated in vacuo and the residue suspended in warm ethyl acetate (70 ml.). The cooled suspension was filtered and the filtrate evaporated in vacuo. The oily residue was suspended in ether and the solid which separated was filtered and crystallised from ethanol to give the title compound (2.17 g.), m.p. 68°-70°. TLC (silica/ether-cyclohexane, 4:1) RF 0.3

Workup

  1. customThe solution was evaporated in vacuo
  2. filtrationThe cooled suspension was filtered
  3. customthe filtrate evaporated in vacuo
  4. customthe solid which separated
  5. filtrationwas filtered
  6. customcrystallised from ethanol

Sources & evidence

ORD record
ord-2ee650e3bb474c7ca696c753f9fbdd11
Source dataset
uspto-grants-1981_04
Patent number
US04264614

Reaction notes

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