Toluene → HCID 136404657, compound

HRID 431445Notes

Reaction equation

HRID 431445 reaction equation
[CH:1](=O)[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.C[NH:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.[P:23]([O-:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26].[C:31]1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([C:1]2[C:21]([CH2:20][N:19]([CH2:18][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[CH3:31])=[CH:22][CH:17]=[CH:16][N:15]=2)[CH:12]=[C:9]([O:10][CH3:11])[C:7]=1[OH:8]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8655SyringaldehydeHCID 883933-(Methylaminomethyl)pyridineHCID 3780918Diethylphosphite

Product 1

HCID 136404657HCID 136404657, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A mixture of 3.0 g (16.5 mmol) of syringaldehyde, 2.03 g (16.6 mmol) of N-methyl-3-picolylamine and 2.3g (16.6 mmol) diethyl phosphite dissolved in 15 ml toluene and a catalytic amount of p-toluenesulfonic acid (ca. 5 mg) contained in a flask connected to a Dean Stark apparatus was refluxed for 2 h. The solution was evaporated and the residue was purified by column chromatography (95/5 CHCl3/MeOH) to yield 3.2 g (46%) of a yellow oil.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe solution was evaporated
  3. customthe residue was purified by column chromatography (95/5 CHCl3/MeOH)

Sources & evidence

ORD record
ord-42511e439eaf4ea4a9291a074582c9e3
Source dataset
uspto-grants-2003_12
Patent number
US06660724B1

Reaction notes

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