Hydrochloric Acid → 2-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acid
Reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:9][CH:8]=1)([O:3]C)=[O:2].[OH-].[Na+].Cl>O>[C:1]([CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:9][CH:8]=1)([OH:3])=[O:2]Participants
Conditions
- Temperature
- 12.5 °C
Procedure
A suspension of 5-[4-[(carbomethoxy)methoxy]benzyl]thiazolidine-2,4-dione obtained by following a procedure described in any of Examples 23-24 (135 g, 0.46 M) and water (540 ml, 4 times w/v) was taken in a round bottom flask fitted with a mechanical stirrer. Aq. sodium hydroxide solution (37 g of NaOH in 135 ml of water) was added slowly over a period of 5-10 minutes at 20-25° C. Stirring was continued at ambient temperature for a period of 2-3 h, while monitoring the reaction by TLC. After the completion of the reaction, the pH of the reaction mixture was adjusted to 2 using conc. HCl (temp. raises to 40-45° C.) and allowed to attain room temperature. The mass was cooled to 10-15° C. and the solid thus obtained was filtered and dried at 60-70° C. under 1-2 mm Hg of vacuum to afford 5-[4-[(carboxy)methoxy]benzyl]thiazolidine-2,4-dione (121 g, Y=99%, P=99.2%).
Workup
- customobtained
- customwas taken in a round bottom flask
- customfitted with a mechanical stirrer
- customthe reaction by TLC
- customAfter the completion of the reaction
- customto attain room temperature
- customthe solid thus obtained
- filtrationwas filtered
- customdried at 60-70° C. under 1-2 mm Hg of vacuum
Sources & evidence
- ORD record
- ord-9af0e96f67c943bca3699cfc16fcfc1e
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06469167B1
Reaction notes
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