Sodium Hydroxide → 3-(4-Nitrophenylthiomethyl)imidazo[1,2-a]pyridine

HRID 856661Notes

Reaction equation

Cl.O[CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]2=[N:6][CH:5]=1.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1)([O-:15])=[O:14].[OH-].[Na+]>C(O)(=O)C.Cl>[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22][CH2:3][C:4]2[N:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]3=[N:6][CH:5]=2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-hydroxymethylimidazo[1,2-a]pyridine hydrochloride (0.50 g) and 4-nitrothiophenol (0.42 g) in acetic acid (10 ml) and concentrated hydrochloric acid (10 ml) was stirred for 5 hours at 100° C. The reaction solution was cooled to 0° C., 8N aqueous solution of sodium hydroxide was added dropwise to adjust pH to 8. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether, to give 3-(4-nitrophenylthiomethyl) imidazo[1,2-a]pyridine (0.54 g) as yellow crystals.

Workup

temperatureThe reaction solution was cooled to 0° C.
extractionThe mixture was extracted with ethyl acetate
washthe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
filtrationThe precipitated crystals were collected by filtration
washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record: ord-caf54881f85d41dca1c371e88fa5daf9
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262185B2

Reaction notes

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