1,1-Bis(methylthio)-2-nitroethylene → N,N'-bis-[2-[[5-[[Hydroxy(methyl)amino]methyl]-2-furanylmethyl]thio]ethyl]-2-nitro-1,1-ethenediamine

HRID 1278007

Reaction equation

HRID 1278007 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[O:10][C:9]([CH2:11][N:12]([OH:14])[CH3:13])=[CH:8][CH:7]=1.CS[C:17](SC)=[CH:18][N+:19]([O-:21])=[O:20]>>[OH:14][N:12]([CH2:11][C:9]1[O:10][C:6]([CH2:5][S:4][CH2:3][CH2:2][NH:1][C:17]([NH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]2[O:10][C:9]([CH2:11][N:12]([OH:14])[CH3:13])=[CH:8][CH:7]=2)=[CH:18][N+:19]([O-:21])=[O:20])=[CH:7][CH:8]=1)[CH3:13]

Participants

3

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 205594295-[[(2-aminoethyl)thio]methyl]-N-hydroxy-N-methyl-2-furanmethanamine

Product 1

HCID 20559448N,N'-bis-[2-[[5-[[Hydroxy(methyl)amino]methyl]-2-furanylmethyl]thio]ethyl]-2-nitro-1,1-ethenediamineYield 45.5%

Procedure

A mixture of 5-[[(2-aminoethyl)thio]methyl]-N-hydroxy-N-methyl-2-furanmethanamine base (1.48 g) and 1,1-bis-(methylthio)-2-nitroethene (0.57 g) was heated at 98°-100° for 3 hr. The oily residue was chromatographed (silica/acetone) and the appropriate eluate evaporated to give the title compound (0.78 g) as an amber oil.

Workup

  1. temperaturewas heated at 98°-100° for 3 hr
  2. customThe oily residue was chromatographed (silica/acetone)
  3. customthe appropriate eluate evaporated

Sources & evidence

ORD record
ord-bf5588ab3dd5479b8d26792bfa48ff60
Source dataset
uspto-grants-1981_07
Patent number
US04279911

Linked notes

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