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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
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Patent
US05700820

Procedure details

A mixture of 70 g of ethyl-3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate, 13.12 g of thiourea and 80.2 ml of sulpholane was reacted for 80 min., under a nitrogen stream at 115°-120° C. Subsequently, a 656.2 ml Acetic acid, 218.7 ml conc. hydrochloric acid and 109.4 ml water was added to this and the resulting mixture was further heated for 12 hrs at 85°-90° C. The reaction mixture was cooled to room temperature and 196.8 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 40 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%. The elution of column was continued further to yield 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl-methoxy)benzyl]2-iminothiazolidine-4-one with HPLC purity of ~70%.
Name
ethyl-3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate
Quantity
70 g
Type
reactant
Reaction Step One
Quantity
13.12 g
Type
reactant
Reaction Step One
Quantity
80.2 mL
Type
reactant
Reaction Step One
Quantity
196.8 g
Type
reactant
Reaction Step Two
Quantity
218.7 mL
Type
reactant
Reaction Step Three
Name
Quantity
109.4 mL
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
C([O:3][C:4](=O)[CH:5](Cl)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2([CH3:32])[CH2:24][CH2:23][C:22]3[C:17](=[C:18]([CH3:31])[C:19]([CH3:30])=[C:20]([O:26]C(=O)C)[C:21]=3[CH3:25])[O:16]2)=[CH:9][CH:8]=1)C.[NH2:35][C:36](N)=[S:37].S1(CCCC1)(=O)=[O:40].Cl.C(=O)(O)[O-].[Na+]>O.C(O)(=O)C>[OH:26][C:20]1[C:21]([CH3:25])=[C:22]2[C:17](=[C:18]([CH3:31])[C:19]=1[CH3:30])[O:16][C:15]([CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH:5]3[S:37][C:36](=[O:40])[NH:35][C:4]3=[O:3])=[CH:12][CH:11]=1)([CH3:32])[CH2:24][CH2:23]2 |f:4.5|

Inputs

Step One
Name
ethyl-3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate
Quantity
70 g
Type
reactant
Smiles
C(C)OC(C(CC1=CC=C(C=C1)OCC1(OC2=C(C(=C(C(=C2CC1)C)OC(C)=O)C)C)C)Cl)=O
Name
Quantity
13.12 g
Type
reactant
Smiles
NC(=S)N
Name
Quantity
80.2 mL
Type
reactant
Smiles
S1(=O)(=O)CCCC1
Step Two
Name
Quantity
196.8 g
Type
reactant
Smiles
C([O-])(O)=O.[Na+]
Step Three
Name
Quantity
218.7 mL
Type
reactant
Smiles
Cl
Name
Quantity
109.4 mL
Type
solvent
Smiles
O
Name
Quantity
656.2 mL
Type
solvent
Smiles
C(C)(=O)O

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
was reacted for 80 min., under a nitrogen stream at 115°-120° C
Duration
80 min
TEMPERATURE
Type
TEMPERATURE
Details
was further heated for 12 hrs at 85°-90° C
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 40 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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