Benzyl Chloride → 4-Benzylthio-1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)pyridinium chloride

HRID 46586Notes

Reaction equation

HRID 46586 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:5](=[S:18])[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:3]1.[CH2:25]([Cl:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1C=CC=CC=1>[Cl-:32].[CH2:25]([S:18][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)=[CH:7][N+:2]([CH3:1])=[CH:3][C:4]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 1812371-Methyl-3-phenyl-5-(3-(trifluoromethyl)phenyl)pyridine-4-thione

Product 1

HCID 233456984-Benzylthio-1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)pyridinium chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.0 g. of 1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinethione and 10 ml. of benzyl chloride in benzene was heated under reflux for 6 hours. The mixture was cooled and the benzene was removed in vacuo. The residue was put on a silica gel column in benzene and the column was flushed with benzene. The product was then removed from the column with denatured ethanol. The ethanol was removed and the residue was crystallized from ether yielding 0.7 g. of 4-benzylthio-1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)pyridinium chloride, m.p. 70°-73°.

Workup

  1. additionA mixture of 2.0 g
  2. temperatureunder reflux for 6 hours
  3. temperatureThe mixture was cooled
  4. customthe benzene was removed in vacuo
  5. customthe column was flushed with benzene
  6. customThe product was then removed from the column with denatured ethanol
  7. customThe ethanol was removed
  8. customthe residue was crystallized from ether yielding 0.7 g

Sources & evidence

ORD record
ord-29ec567dce774185bea2d359c3e4c5f8
Source dataset
uspto-grants-1979_11
Patent number
US04174209

Reaction notes

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