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molecular formula C19H20N2O3S B8692418 (R)-Pioglitazone CAS No. 959687-65-1

(R)-Pioglitazone

Cat. No. B8692418
M. Wt: 356.4 g/mol
InChI Key: HYAFETHFCAUJAY-QGZVFWFLSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
USRE036575

Procedure details

To a dimethylformamide solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (1.0 g) was added palladium black (0.2 g) and catalytic reduction was carried out at 50° C. and 50 kg/cm2 for 5 hours. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was dissolved in 6N-hydrochloric acid and the solution was neutralized with sodium hydrogen carbonate to give 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione as crystals. Yield: 650 mg (64.8%); m.p.: 173°-174° C.
Quantity
1 g
Type
reactant
Reaction Step One
Quantity
0.2 g
Type
catalyst
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]>[Pd].CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]

Inputs

Step One
Name
Quantity
1 g
Type
reactant
Smiles
C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1
Name
Quantity
0.2 g
Type
catalyst
Smiles
[Pd]
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CN(C=O)C

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
was carried out at 50° C.
FILTRATION
Type
FILTRATION
Details
The catalyst was filtered off
CONCENTRATION
Type
CONCENTRATION
Details
the filtrate was concentrated to dryness
DISSOLUTION
Type
DISSOLUTION
Details
The residue was dissolved in 6N-hydrochloric acid

Outcomes

Product
Details
Reaction Time
5 h
Name
Type
product
Smiles
C(C)C=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1

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.
Patent
USRE036575

Procedure details

To a dimethylformamide solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (1.0 g) was added palladium black (0.2 g) and catalytic reduction was carried out at 50° C. and 50 kg/cm2 for 5 hours. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was dissolved in 6N-hydrochloric acid and the solution was neutralized with sodium hydrogen carbonate to give 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione as crystals. Yield: 650 mg (64.8%); m.p.: 173°-174° C.
Quantity
1 g
Type
reactant
Reaction Step One
Quantity
0.2 g
Type
catalyst
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]>[Pd].CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]

Inputs

Step One
Name
Quantity
1 g
Type
reactant
Smiles
C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1
Name
Quantity
0.2 g
Type
catalyst
Smiles
[Pd]
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CN(C=O)C

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
was carried out at 50° C.
FILTRATION
Type
FILTRATION
Details
The catalyst was filtered off
CONCENTRATION
Type
CONCENTRATION
Details
the filtrate was concentrated to dryness
DISSOLUTION
Type
DISSOLUTION
Details
The residue was dissolved in 6N-hydrochloric acid

Outcomes

Product
Details
Reaction Time
5 h
Name
Type
product
Smiles
C(C)C=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1

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.
Patent
USRE036575

Procedure details

To a dimethylformamide solution of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione (1.0 g) was added palladium black (0.2 g) and catalytic reduction was carried out at 50° C. and 50 kg/cm2 for 5 hours. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was dissolved in 6N-hydrochloric acid and the solution was neutralized with sodium hydrogen carbonate to give 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione as crystals. Yield: 650 mg (64.8%); m.p.: 173°-174° C.
Quantity
1 g
Type
reactant
Reaction Step One
Quantity
0.2 g
Type
catalyst
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]>[Pd].CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]

Inputs

Step One
Name
Quantity
1 g
Type
reactant
Smiles
C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C2C(NC(S2)=O)=O)C=C1
Name
Quantity
0.2 g
Type
catalyst
Smiles
[Pd]
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CN(C=O)C

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
was carried out at 50° C.
FILTRATION
Type
FILTRATION
Details
The catalyst was filtered off
CONCENTRATION
Type
CONCENTRATION
Details
the filtrate was concentrated to dryness
DISSOLUTION
Type
DISSOLUTION
Details
The residue was dissolved in 6N-hydrochloric acid

Outcomes

Product
Details
Reaction Time
5 h
Name
Type
product
Smiles
C(C)C=1C=CC(=NC1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1

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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