4-(Chloromethyl)pyridinium chloride → HCID 13503211, compound

HRID 256309Notes

Reaction equation

HRID 256309 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10]3=[C:11]([N:13]=[C:14]([SH:15])[N:9]3[CH2:8][CH2:7][CH2:6]2)[CH:12]=1.Cl.[N:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][CH:18]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10]3=[C:11]([N:13]=[C:14]([S:15][CH2:23][C:20]4[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=4)[N:9]3[CH2:8][CH2:7][CH2:6]2)[CH:12]=1

Participants

4

Reactant 2

HCID 745704-(Chloromethyl)pyridinium chlorideHCID 178486387HCID 178486387, compound

Product 1

HCID 13503211HCID 13503211, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5,6-dihydro-8-methoxy-2-mercapto-4H-imidazo[4,5,1-ij]quinoline (2.2 g) in ethanol was added 4-picolyl chloride HCl (1.68 g) and the mixture was stirred at ambient temperature for 16 hours and at reflux for 2 hours. The solvent was removed by evaporation and the residue dissolved in water. The solution was washed with EtOAc and then basified (aqueous NaOH) and extracted with CHCl3. Following short column chromatography (SiO2 /CHCl3) the residue was crystallised from EtOAc to give the title compound (1.45 g, 43%) mp 99°-101° C. (Found: C,65.55; H,5.6; N,13.8. C17H17N3OS, requires C,65.6; H,5.5; N,13.5%).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed by evaporation
  3. dissolutionthe residue dissolved in water
  4. washThe solution was washed with EtOAc
  5. extractionextracted with CHCl3
  6. customwas crystallised from EtOAc

Sources & evidence

ORD record
ord-ab4edf7a218443a886e7dbb03e1b32ac
Source dataset
uspto-grants-1987_10
Patent number
US04703044

Reaction notes

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