Hydrochloric Acid → 2-(Imidazo[1,2-b]pyridazin-6-ylthio)benzoic acid

HRID 2391561Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 2-(imidazo[1,2-b]pyridazin-6-ylthio)benzoate (619 mg, 2.17 mmol) in methanol (20 mL) was added 8N aqueous sodium hydroxide solution (1.00 mL), and the mixture was stirred at 70° C. for 18 hr. After the reaction mixture was allowed to cool to room temperature, 6N hydrochloric acid (1.33 mL) was added to the reaction mixture, and the precipitated precipitate was collected by filtration, and washed with water. The precipitate was suspended in methanol (10 mL), and the suspension was stirred with heating under reflux for 10 min. After the suspension was allowed to cool to room temperature, the precipitate was collected by filtration, washed with methanol, and dried under reduced pressure to give the title compound (496 mg, 1.83 mmol, yield 84%) as a white solid.

Workup

temperatureto cool to room temperature
filtrationthe precipitated precipitate was collected by filtration
washwashed with water
stirringthe suspension was stirred
temperaturewith heating
temperatureunder reflux for 10 min
temperatureto cool to room temperature
filtrationthe precipitate was collected by filtration
washwashed with methanol
customdried under reduced pressure

Sources & evidence

ORD record: ord-d80f9f452e2a450da8547d35cc12f93c
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273741B2

Reaction notes

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