Methylamine → HCID 67621995, compound

HRID 1734130Notes

Reaction equation

HRID 1734130 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH:7][C:8](SC)=[CH:9][N+:10]([O-:12])=[O:11])[CH2:2]1.[CH3:15][NH2:16]>CO.[OH-].[Na+].C(O)C>[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH:7][C:8]([NH:16][CH3:15])=[CH:9][N+:10]([O-:12])=[O:11])[CH2:2]1

Participants

6

Reactant 2

HCID 6329MethylamineHCID 67619523HCID 67619523, compound

Product 1

HCID 67621995HCID 67621995, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture comprising 7.0 g of (tetrahydro-3-furanyl)methylamine, 12.5 g of 1,1-bis(methylthio)-2-nitroethylene and 100 ml of acetonitrile was refluxed for 5 hours. The reaction mixture was concentrated under a reduced pressure, and purified by silica gel column chromatography (eluent:ethyl acetate/hexane=1/1) to give 6.6 g of 1-[{tetrahydro-3-furanyl)methyl}amino]-1-methylthio-2-nitroethylene. Then, a mixture comprising 4.0 g of the 1-[{(tetrahydro-3-furanyl)methyl}amino]-1-methylthio-2-nitroethylene obtained above, 6.0 ml of 40% methylamine in methanol solution, 20 ml of 1N aqueous sodium hydroxide solution and 20 ml of ethanol was stirred at room temperature for 5 hours. The resulting reaction mixture was concentrated under a reduced pressure, and purified by silica gel column chromatography (eluent:ethyl acetate/methanol=9/1) to obtain 3.2 g of 1-[{(tetrahydro-3-furanyl)methyl}amino]-1-methylamino-2-nitroethylene.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under a reduced pressure
  3. custompurified by silica gel column chromatography (eluent:ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-06a0f64b6e1e40408c369dd9ddb09148
Source dataset
uspto-grants-1996_07
Patent number
US05532365

Reaction notes

Loading…