1,2-Dichloroethane → 1-(2-Chloroethyl)pyridin-1-ium chloride

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:7][CH2:8][CH2:9]Cl>>[Cl-:7].[Cl:7][CH2:8][CH2:9][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 111,2-Dichloroethane

HCID 1049Pyridine

Product 1

HCID 233368841-(2-Chloroethyl)pyridin-1-ium chloride

Procedure

A solution of pyridine (100 g, 1.25 mole) in 800 ml. of 1,2-dichloroethane was refluxed for 72 hours. The white crystalline material which formed was filtered, washed repeatedly with fresh 1,2-dichloroethane and dried. Collected 200 g (89 per cent yield), nmr (D2O) ppm (δ), 4.3 (t, 3), 5.6 (t, 3), 8.1 - 9.3 (m, 5).

Workup

customThe white crystalline material which formed
filtrationwas filtered
washwashed repeatedly with fresh 1,2-dichloroethane
customdried
customCollected
custom200 g (89 per cent yield), nmr (D2O) ppm (δ), 4.3 (t, 3), 5.6 (t, 3), 8.1 - 9.3 (m, 5)

Sources & evidence

ORD record: ord-8ed2974d5a154a28860d5ee2995b100c
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04010156

Reaction notes

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