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molecular formula C24H27NO5S B1681588 Troglitazone CAS No. 97322-87-7

Troglitazone

Cat. No. B1681588
M. Wt: 441.5 g/mol
InChI Key: GXPHKUHSUJUWKP-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US05700820

Procedure details

15.5 g of 5-[4-(6-hydroxy-2,5,7,8-tetramethyl chroman-2-yl-methoxy) benzyl]-2-iminothiazolidine-4-one, prepared by the process as described in Example-1, was added to a mixture of 225 ml of acetic acid, 75 ml of conc. hydrochloric acid and 40 ml of water and the mixture was refluxed for 12 hrs. The reaction mixture was cooled to room temperature and 66.2 g of sodium bicarbonate was added and once the evolution of carbondioxide had ceased, the solvent was distilled off applying high vacuum. A 10:1 by volume mixture of benzene and ethyl acetate was added to the residue and the crude product was washed with a mixture of equal volumes of a saturated aq. sodium bicarbonate solution & water. The organic layer was dried over anhydrous sodium sulphate and the solvent was distilled off. The resulting crude product was quickly eluted from a silica gel column with 50% ethylacetate-hexane to furnish 12.5 g of the required 5-{4-(6-hydroxy-2, 5, 7, 8-tetramethylchroman-2-yl-methoxy) benzyl) thiazolidine-2,4-dione (Troglitazone) with a HPLC purity of ~67-70%.
Name
5-[4-(6-hydroxy-2,5,7,8-tetramethyl chroman-2-yl-methoxy) benzyl]-2-iminothiazolidine-4-one
Quantity
15.5 g
Type
reactant
Reaction Step One
Quantity
225 mL
Type
reactant
Reaction Step Two
Quantity
75 mL
Type
reactant
Reaction Step Two
Name
Quantity
40 mL
Type
solvent
Reaction Step Two
Quantity
66.2 g
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=N)[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2.C(O)(=[O:34])C.Cl.C(=O)(O)[O-].[Na+]>O>[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:34])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2 |f:3.4|

Inputs

Step One
Name
5-[4-(6-hydroxy-2,5,7,8-tetramethyl chroman-2-yl-methoxy) benzyl]-2-iminothiazolidine-4-one
Quantity
15.5 g
Type
reactant
Smiles
OC=1C(=C2CCC(OC2=C(C1C)C)(C)COC1=CC=C(CC2C(NC(S2)=N)=O)C=C1)C
Step Two
Name
Quantity
225 mL
Type
reactant
Smiles
C(C)(=O)O
Name
Quantity
75 mL
Type
reactant
Smiles
Cl
Name
Quantity
40 mL
Type
solvent
Smiles
O
Step Three
Name
Quantity
66.2 g
Type
reactant
Smiles
C([O-])(O)=O.[Na+]

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
the mixture was refluxed for 12 hrs
Duration
12 h
DISTILLATION
Type
DISTILLATION
Details
the solvent was distilled off
ADDITION
Type
ADDITION
Details
A 10:1 by volume mixture of benzene and ethyl acetate
ADDITION
Type
ADDITION
Details
was added to the residue
WASH
Type
WASH
Details
the crude product was washed with a mixture of equal volumes of a saturated aq. sodium bicarbonate solution & water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The organic layer was dried over anhydrous sodium sulphate
DISTILLATION
Type
DISTILLATION
Details
the solvent was distilled off
WASH
Type
WASH
Details
The resulting crude product was quickly eluted from a silica gel column with 50% ethylacetate-hexane

Outcomes

Product
Name
Type
product
Smiles
OC=1C(=C2CCC(OC2=C(C1C)C)(C)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)C
Measurements
Type Value Analysis
AMOUNT: MASS 12.5 g

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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