1,1-Bis(methylthio)-2-nitroethylene → HCID 86746463, compound

HRID 1645934Notes

Reaction equation

HRID 1645934 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:24])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:3][CH2:4][S:5][CH2:6][CH2:7][NH2:8].[CH3:25][S:26][C:27](SC)=[CH:28][N+:29]([O-:31])=[O:30]>C(#N)C>[CH3:25][S:26][C:27]([NH:8][CH2:7][CH2:6][S:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:24])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:28][N+:29]([O-:31])=[O:30]

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 54561366HCID 54561366, compound

Product 1

HCID 86746463HCID 86746463, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ylthio)ethylamine (14.0 g, 40.0 mmol, prepared as described in Example 5) and 1,1-bis(methylthio)-2-nitroethylene (6.60 g, 40.0 mmol) in 100 ml of acetonitrile was heated at reflux temperature for 5 hours. The reaction mixture was evaporated in vacuo to dryness and the remaining residue was chromatographed on silica gel, eluting with CHCl3 /MeOH (200:1) to afford 14.7 g (78.6%) of the desired compound, as a pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 hours
  3. customThe reaction mixture was evaporated in vacuo to dryness
  4. customthe remaining residue was chromatographed on silica gel
  5. washeluting with CHCl3 /MeOH (200:1)

Sources & evidence

ORD record
ord-14131cabfd514042a19c58deca1907b7
Source dataset
uspto-grants-1993_01
Patent number
US05177102

Reaction notes

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