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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
US04572912

Procedure details

3.1 g of 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one [prepared as described in Example 1(a)] were added to a mixture of 45 ml of acetic acid, 15 ml of concentrated hydrochloric acid and 8 ml of water, and the mixture was reacted for 12 hours at 85°-90° C. It was then processed and purified in a similar manner to Example 1(a), giving 2.5 g of 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione, whose melting point and nuclear magnetic resonance spectrum were consistent with those of the product of Example 1(b).
Name
5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one
Quantity
3.1 g
Type
reactant
Reaction Step One
Quantity
45 mL
Type
reactant
Reaction Step One
Quantity
15 mL
Type
reactant
Reaction Step One

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>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

Inputs

Step One
Name
5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one
Quantity
3.1 g
Type
reactant
Smiles
OC=1C(=C2CCC(OC2=C(C1C)C)(C)COC1=CC=C(CC2C(NC(S2)=N)=O)C=C1)C
Name
Quantity
45 mL
Type
reactant
Smiles
C(C)(=O)O
Name
Quantity
15 mL
Type
reactant
Smiles
Cl
Name
Quantity
8 mL
Type
solvent
Smiles
O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
the mixture was reacted for 12 hours at 85°-90° C
Duration
12 h
CUSTOM
Type
CUSTOM
Details
purified in a similar manner to Example 1(a)

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 2.5 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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