Hydrochloric Acid → Rosiglitazone hydrochloride

HRID 1791379Notes

Reaction equation

[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:23])=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[ClH:26]>CC(O)C>[ClH:26].[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:23])=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (6.0 g) and propan-2-ol (120 ml) was stirred and heated to 50° C. under a nitrogen atmosphere. A solution of hydrogen chloride in propan-2-ol (5-6 N, 5.0 ml) was added and the stirred mixture warmed to 70° C., at which point a clear solution was observed. After cooling to 45° C. over a period of one hour the resulting cloudy solution was warmed to 60° C. and maintained at this temperature for a period of 1 hour. The resulting thick white suspension was cooled to 30° C. and the solid product collected by filtration, washed with propan-2-ol (25 ml) and dried under vacuum, over phosphorus pentoxide for 16 hours to give the title compound as a white crystalline solid (5.7 g).

Workup

temperaturethe stirred mixture warmed to 70° C., at which point a clear solution
temperatureAfter cooling to 45° C. over a period of one hour the resulting cloudy solution
temperaturewas warmed to 60° C.
temperaturemaintained at this temperature for a period of 1 hour
temperatureThe resulting thick white suspension was cooled to 30° C.
filtrationthe solid product collected by filtration
washwashed with propan-2-ol (25 ml)
dry with materialdried under vacuum, over phosphorus pentoxide for 16 hours

Sources & evidence

ORD record: ord-c7f2c59b0c024907b116881ff0d47bac
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074811B2

Reaction notes

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