Synthesis routes of Troglitazone

Troglitazone

Número de catálogo B1681588

: 97322-87-7

Peso molecular: 441.5 g/mol

Clave InChI: GXPHKUHSUJUWKP-UHFFFAOYSA-N

Atención: Solo para uso de investigación. No para uso humano o veterinario.

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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

Name

acetic acid

Quantity

45 mL

Type

reactant

Reaction Step One

Name

hydrochloric acid

Quantity

15 mL

Type

reactant

Reaction Step One

Name

water

Quantity

8 mL

Type

solvent

Reaction Step One

Name

5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

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	acetic acid
Quantity	45 mL
Type	reactant
Smiles	C(C)(=O)O

Name	hydrochloric acid
Quantity	15 mL
Type	reactant
Smiles	Cl

Name	water
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	5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione
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

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.