Toluene → HCID 136404656, compound

HRID 431444Notes

Reaction equation

HRID 431444 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.[N:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16]C=1.[P:22]([O-:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25].[C:30]1(C)C=CC=CC=1>>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([C:1]2[CH:16]=[C:17]([CH2:20][NH:21][CH2:30][P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])[CH:18]=[CH:19][N:14]=2)[CH:12]=[C:9]([O:10][CH3:11])[C:7]=1[OH:8]

Participants

5

Reactant 4

HCID 1140TolueneHCID 8655SyringaldehydeHCID 773174-PyridinemethanamineHCID 3780918Diethylphosphite

Product 1

HCID 136404656HCID 136404656, compoundYield 45%

Procedure

A solution of 2.5 g (13.7 mmol) syringaldehyde and 1.6 g (14.4 mmol) 4-picolylamine dissolved in 100 ml toluene contained in a flask connected to a Dean-Stark apparatus was refluxed for 3 h. Toluene was evaporated under vacuum then the residue dissolved in 10 ml THF was heated with 5.1 g (36.8 mmol) diethyl phosphite for 6 h. THF was evaporated and the residue was purified by column chromatography (SiO2, 95/5 CHCl3/MeOH). Recrystallisation in a mixture of CH2Cl2-petroleum ether gave 3.7 g (45%) of a solid, mp=124-126° C.

Workup

  1. customcontained in a flask
  2. temperaturewas refluxed for 3 h
  3. customToluene was evaporated under vacuum
  4. dissolutionthe residue dissolved in 10 ml THF
  5. customTHF was evaporated
  6. customthe residue was purified by column chromatography (SiO2, 95/5 CHCl3/MeOH)
  7. customRecrystallisation
  8. additionin a mixture of CH2Cl2-petroleum ether

Sources & evidence

ORD record
ord-3cbb0e1a49a4400eb43d9efab8df1f76
Source dataset
uspto-grants-2003_12
Patent number
US06660724B1

Reaction notes

Loading…