Benzyl Bromide → 1-Benzyl-2-(benzylsulfanyl)pyridin-1-ium bromide

HRID 1758818Notes

Reaction equation

HRID 1758818 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([Br:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCOCC>[Br-:22].[CH2:15]([N+:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 4729612-benzylsulfanylpyridine

Product 1

HCID 134350011-Benzyl-2-(benzylsulfanyl)pyridin-1-ium bromideYield 59.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(benzylthio)pyridine (2.01 g) and benzyl bromide (1.71 g) was kept at ambient temperature for 4 days. Trituration at length with ether gave a solid which was removed by filtration and dried to give the title compound (2.2 g) mp 125°-7° C. (Found: C, 61.6; H, 5.2; N, 3.6%. C19H18BrNS requires C, 61.3; H, 4.9; N, 3.8%).

Workup

  1. customwas removed by filtration
  2. customdried

Sources & evidence

ORD record
ord-7edb2e045f0f4ee5a2e38c7cc20fbd14
Source dataset
uspto-grants-1983_02
Patent number
US04374992

Reaction notes

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