p-Toluenesulfonic acid → HCID 5325127, compound

HRID 1271836Notes

Reaction equation

HRID 1271836 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[NH2:9][CH:10]([P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])[P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:9][CH:10]([P:11](=[O:18])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17])[P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 142732-PyridinecarboxaldehydeHCID 2773808Tetraethyl aminomethylenediphosphonate

Product 1

HCID 5325127HCID 5325127, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-pyridinecarboxaldehyde (1.23 g, 11.5 mmol), tetraethyl aminomethylenediphosphonate (3.0 g, 9.9 mmol) and a catalytic amount of p-toluenesulfonic acid dissolved in 10 ml toluene was heated to reflux for 7 h. Toluene was evaporated and the residue dissolved in ethanol was submitted for 12 h to catalytic hydrogenation with 10% palladium on charcoal. Ethanol was evaporated and the title compound was obtained as an oil (1.30 g, 33%) by column chromatography (silica gel, CH2Cl2/MeOH 9/1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 h
  3. customToluene was evaporated
  4. dissolutionthe residue dissolved in ethanol
  5. customEthanol was evaporated

Sources & evidence

ORD record
ord-069c1515e5c646aebf575bb95e03a71b
Source dataset
uspto-grants-2007_04
Patent number
US07208481B2

Reaction notes

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