Imidazole → 2-Chloro-3-cyano-6-(imidazol-1-yl)-4-methylpyridine

HRID 53552

Reaction equation

HRID 53552 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4](Cl)[N:3]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.C(Cl)(Cl)Cl.C(O)C>CN(C)C=O>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[N:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 701313-Cyano-2,6-dichloro-4-methylpyridineHCID 21889567Chloroform ethanol

Product 1

HCID 199600342-Chloro-3-cyano-6-(imidazol-1-yl)-4-methylpyridineYield 22.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,6-dichloro-3-cyano-4-methylpyridine (5.6 g) and imidazole (2.04 g) in dimethylformamide (10 mL) was heated at 130° C. for 1.25 hours. After cooling to room temperature the mixture was fractionated directly on silica gel with chloroform/ethanol gradient) to give 1.5 g of the title compound, suitable for use in the next reaction.

Sources & evidence

ORD record
ord-25680b9d2119456ca39879f14ba8ca68
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Linked notes

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