2-Chloropyridine → 4-Methoxybenzyl-2-chloropyridinium hexafluoroantimonate

HRID 1460264Notes

Reaction equation

HRID 1460264 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[F:18][Sb-:19]([F:24])([F:23])([F:22])([F:21])[F:20].[Na+]>CO>[F:18][Sb-:19]([F:24])([F:23])([F:22])([F:21])[F:20].[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N+:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 79772-ChloropyridineHCID 699934-Methyloxybenzyl chlorideHCID 16689647Sodium hexafluoroantimonate

Product 1

HCID 167053924-Methoxybenzyl-2-chloropyridinium hexafluoroantimonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4,698 g (0.03 mol) of 4-methoxybenzyl chloride and 10.22 g (0.09 mol) of 2-chloropyridine were reacted in 40 ml of methanol at 40° C. for 3 days. After the reaction, the solvent was evaporate in vacuo and ether-water was added to the residue to extract unreacted reactants in the etherial layer. To the aqueous layer containing the pyridinium chloride was added 7.764 g (0.03 mol) of sodium hexafluoroantimonate. The resulting crystals were suction filtered, washed and dried to give the title compound melting at 122°-124° C.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporate in vacuo and ether-water
  3. additionwas added to the residue
  4. extractionto extract unreacted reactants in the etherial layer
  5. additionTo the aqueous layer containing the pyridinium chloride
  6. filtrationfiltered
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-673c9175f8d040c08ae4b10c9e5a3886
Source dataset
uspto-grants-1991_12
Patent number
US05070161

Reaction notes

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