1,1-Bis(methylthio)-2-nitroethylene → HCID 178503826, compound

HRID 597393Notes

Reaction equation

HRID 597393 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[N+:12]([CH:15]=[C:16](SC)[S:17][CH3:18])([O-:14])=[O:13]>C(O)(C)(C)C.C(#N)C>[N+:12]([CH:15]=[C:16]([S:17][CH3:18])[NH:11][CH2:10][CH2:9][S:8][CH2:7][C:6]1[NH:5][CH:4]=[N:3][C:2]=1[CH3:1])([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 178433288HCID 178433288, compound

Product 1

HCID 178503826HCID 178503826, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]-imidazole (1.71 g) in t-butanol (30 ml) was added slowly to a solution of 1-nitro-2,2-bis methylthioethylene (1.66 g) in acetonitrile (20 ml) at room temperature. The solution was heated under reflux for 3 hours, evaporated to dryness and chromatographed on a column of silica gel with elution by anhydrous ether (250 ml) followed by acetone (500 ml). The acetone eluate was concentrated to low bulk to give 1-nitro-2-methylthio-2-[2-((4-methyl-5-imidazolyl)methylthio)ethylamino]-ethylene (1.58 g), m.p. 151°-153°. A sample recrystallised from acetonitrile had m.p. 152°-153°.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 3 hours
  3. customevaporated to dryness
  4. customchromatographed on a column of silica gel with elution by anhydrous ether (250 ml)
  5. concentrationThe acetone eluate was concentrated to low bulk

Sources & evidence

ORD record
ord-d629152a48cf41d996205a0535027d09
Source dataset
uspto-grants-1977_03
Patent number
US04013769

Reaction notes

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