Ethanol → HCID 9911750, compound

HRID 1591951Notes

Reaction equation

HRID 1591951 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.C(O)C>C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6395Methanesulfonic AcidHCID 77999Rosiglitazone

Product 1

HCID 9911750HCID 9911750, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
21 °C

Procedure

Methanesulfonic acid (1.69 g) was added to a suspension of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (6.0 g) and ethanol (50 ml) and the mixture was stirred and heated to give a clear solution. Diethyl ether (50 ml) was added and the mixture was heated to reflux and then cooled to 21° C. over a period of 1 hour. The product was collected by filtration, washed with diethyl ether (50 ml) and dried under vacuum for 2 hours at 21° C. to give 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione methanesulfonate (6.40 g) as a white crystalline solid.

Workup

  1. temperatureheated
  2. customto give a clear solution
  3. temperaturethe mixture was heated
  4. temperatureto reflux
  5. filtrationThe product was collected by filtration
  6. washwashed with diethyl ether (50 ml)
  7. customdried under vacuum for 2 hours at 21° C.

Sources & evidence

ORD record
ord-a86b5272f43249bba3da29fd1b6b9bcd
Source dataset
uspto-grants-2007_11
Patent number
US07291740B2

Reaction notes

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