1,1-Bis(methylthio)-2-nitroethylene → 1-Nitro-2-methylthio-2-[4-(4-imidazolyl)butylamino]ethylene

HRID 67917Notes

Reaction equation

HRID 67917 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][CH:10]=1.[N+:11]([CH:14]=[C:15](SC)[S:16][CH3:17])([O-:13])=[O:12]>C(#N)C>[N+:11]([CH:14]=[C:15]([S:16][CH3:17])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 178510959HCID 178510959, compound

Product 1

HCID 1785038211-Nitro-2-methylthio-2-[4-(4-imidazolyl)butylamino]ethylene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(4-aminobutyl)imidazole (from the dihydrobromide 3.6 g) and 1-nitro-2,2-bis-methylthioethylene (2.0 g) in acetonitrile (50 ml) is set aside at room temperature for 3 days. The produce is chromatographed on a column of silica gel with elution by ethyl acetate to give 1-nitro-2-methylthio-2-[4-(4-imidazolyl)butylamino]ethylene. Reaction of this methylthio compound with hydrazine hydrate in the procedure of Example 3 results in the production of 1-nitro-2-[4-(4-imidazolyl)butylamino]-2-hydrazinoethylene.

Workup

  1. customThe produce is chromatographed on a column of silica gel with elution by ethyl acetate

Sources & evidence

ORD record
ord-d50b2b5c417c403593ca650ecf4ec911
Source dataset
uspto-grants-1982_08
Patent number
US04347250

Reaction notes

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