Hydrochloric Acid → Rosiglitazone hydrochloride

HRID 1791380Notes

Reaction equation

HRID 1791380 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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 77999Rosiglitazone

Product 1

HCID 9865387Rosiglitazone hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (4.0 g) and propan-2-ol (100 ml) was stirred and heated to 70° C. Concentrated hydrochloric acid (1.1 ml) was added to the stirred reaction mixture which was observed to give a clear solution after approximately 3 minutes. The stirred solution was cooled to 58° C. and then maintained at a temperature between 58-60° C. for 1 hour. The resulting white suspension was cooled to 30° C. and the solid product collected by filtration, washed with propan-2-ol (20 ml) and dried under vacuum over phosphorus pentoxide for 64 hours to give the title compound as a white crystalline solid (4.3 g).

Workup

  1. customto give a clear solution after approximately 3 minutes
  2. temperatureThe stirred solution was cooled to 58° C.
  3. temperaturemaintained at a temperature between 58-60° C. for 1 hour
  4. temperatureThe resulting white suspension was cooled to 30° C.
  5. filtrationthe solid product collected by filtration
  6. washwashed with propan-2-ol (20 ml)
  7. dry with materialdried under vacuum over phosphorus pentoxide for 64 hours

Sources & evidence

ORD record
ord-ea9123fbb35a4123bac91acc28583f4b
Source dataset
uspto-grants-2006_07
Patent number
US07074811B2

Reaction notes

Loading…