Sodium Phosphate, Dibasic → HCID 67930873, compound

HRID 728578Notes

Reaction equation

HRID 728578 reaction equation
[CH2:1]([N:5]([C:7](SC)=[CH:8][N+:9]([O-:11])=[O:10])[CH3:6])[CH2:2][CH2:3][CH3:4].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH2:21])[CH:15]=1.P([O-])([O-])(O)=O.[Na+].[Na+]>C(O)C>[CH2:1]([N:5]([C:7]([NH:21][CH2:20][C:16]1[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=1)=[CH:8][N+:9]([O-:11])=[O:10])[CH3:6])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 310183-PyridinemethanamineHCID 54165061HCID 54165061, compound

Product 1

HCID 67930873HCID 67930873, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.2 g of 2-(N-n-butyl-N-methylamino)-2-methylthio-1-nitroethylene, 2.84 g of pyridin-3-ylmethylamine and 3.69 g of disodium hydrogen phosphate in 30 ml of ethanol is refluxed for 1 hour. After removing the salt by filtration, the solvent is evaporated from the solution under vacuum and the residue is chromatographed through a column of silica gel with a 95/5 mixture of ethyl acetate/methanol. The product is eluated with ethylacetate/methanol (85/15). The solvent is removed by evaporation, affording 3.7 g of 2-(N-n-butyl-N-methylamino)-2-(pyridin-3-ylmethylamino)-1-nitroethylene as a viscous oil (Compound 3.2, Table 3).

Workup

  1. temperatureis refluxed for 1 hour
  2. customAfter removing the salt
  3. filtrationby filtration
  4. customthe solvent is evaporated from the solution under vacuum
  5. customthe residue is chromatographed through a column of silica gel with a 95/5 mixture of ethyl acetate/methanol
  6. customThe solvent is removed by evaporation

Sources & evidence

ORD record
ord-6b6c071f92a84fd7a8a9482111f058dd
Source dataset
uspto-grants-1991_09
Patent number
US05049571

Reaction notes

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