Thionyl Chloride → 5,6-Dichloro-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine

Reaction equation

O[N:2]1[C:10]2[C:5](=[N:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4]=[C:3]1[C:12]([F:15])([F:14])[F:13].S(Cl)([Cl:18])=O>>[Cl:11][C:7]1[N:6]=[C:5]2[N:4]=[C:3]([C:12]([F:15])([F:14])[F:13])[NH:2][C:10]2=[CH:9][C:8]=1[Cl:18]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 20355533HCID 20355533, compound

Product 1

HCID 215569715,6-Dichloro-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine

Procedure

1-Hydroxy-5-chloro-2-(trifluoromethyl)-1H-imidazo [4,5-b] pyridine (100 milligrams) was mixed with 10milliliters of thionyl chloride and the mixture refluxed on a steam bath for ten hours. The thionyl chloride was then evaporated and the residue, the desired 5,6-dichloro-2-(trifluoromethyl) -1H-imidazo [4,5-b] pyridine product, was shaken with water and separated by filtration, m.p. 222° -24° C.

Workup

temperaturethe mixture refluxed on a steam bath for ten hours
customThe thionyl chloride was then evaporated
customseparated by filtration, m.p. 222° -24° C.

Sources & evidence

ORD record: ord-7f16efa904814483ada2cdd69bf44621
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04031107

Reaction notes

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