4-Nitrobenzyl bromide → 2-(Benzylsulfanyl)-1-[(4-nitrophenyl)methyl]pyridin-1-ium bromide

HRID 1758816Notes

Reaction equation

HRID 1758816 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][Br:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:12]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(C)=O>[Br-:9].[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N+:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[S:19][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 4729612-benzylsulfanylpyridine

Product 1

HCID 134350032-(Benzylsulfanyl)-1-[(4-nitrophenyl)methyl]pyridin-1-ium bromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-nitrobenzyl bromide (1.08 g) and 2-(benzylthio)pyridine (1.05 g) were heated at 100° C. for 4 hours and cooled. Crystals which formed on trituration with acetone were removed by filtration and dried to give the title compound as a quarter hydrate (1.6 g) mp 160°-2° C. (Found C, 53.8; H, 4.5; N, 6.4%. C19H17BrN2O2S1/4H2O requires C, 54.1; H, 4.2; N, 6.6%).

Workup

  1. temperaturecooled
  2. customwere removed by filtration
  3. customdried

Sources & evidence

ORD record
ord-1baedb14714b4f67b7e6510f83265156
Source dataset
uspto-grants-1983_02
Patent number
US04374992

Reaction notes

Loading…