Thionyl Chloride → 2,3-Dichloro-5-(chloromethyl)pyridine

HRID 1701749

Reaction equation

HRID 1701749 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9]O)=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>>[Cl:13][CH2:9][C:5]1[CH:6]=[C:7]([Cl:8])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 101765362,3-Dichloro-5-(chloromethyl)pyridine

Procedure

2,3-Dichloro-5-hydroxymethyl-pyridine is reacted in a known manner with thionyl chloride to give 5-chloromethyl-2,3-dichloro-pyridine and the latter is reacted with sodium cyanide, without additional purification (for example analogously to L. A. Carlson et al., Acta Pharm. Suecica 9, 411 (1972)). 5,6-Dichloro-pyridine-3-acetonitrile, thus obtained, melts at 72°-75° C. after recrystallisation from ether.

Sources & evidence

ORD record
ord-094b3d4c72d5409c841d749bec1227c2
Source dataset
uspto-grants-1980_03
Patent number
US04195090

Linked notes

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