Troglitazone
Katalognummer B1681588
Molekulargewicht: 441.5 g/mol
InChI-Schlüssel: GXPHKUHSUJUWKP-UHFFFAOYSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
Patent
US05104888
Procedure details
A mixture of 9.6 g of ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate (prepared as described in Preparation 51), 1.8 g of thiourea and 11 ml of sulfolane was heated for 3.5 hours at 120° C. under a nitrogen stream. 100 ml of ethylene glycol monomethyl ether and 70 ml of 10% w/v aqueous hydrochloric acid were then added to the reaction mixture, after which it was heated under reflux for 12 hours. The product was then purified as described in Example 27, to give the title compound. The melting point and nuclear magnetic resonance spectrum of this compound accorded with those of the compound obtained in Example 27(b).
Name
ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate
Quantity
9.6 g
Type
reactant
Reaction Step One
Name
Identifiers
|
REACTION_CXSMILES
|
C([O:4][C:5]1[C:6]([CH3:34])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27](Cl)[C:28](OCC)=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][CH2:8]2)(=O)C.[NH2:35][C:36](N)=[S:37].S1(CCCC1)(=O)=[O:40].Cl>COCCO>[OH:4][C:5]1[C:6]([CH3:34])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27]3[S:37][C:36](=[O:40])[NH:35][C:28]3=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][CH2:8]2
|
Inputs
Step One
|
Name
|
ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate
|
|
Quantity
|
9.6 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C)(=O)OC=1C(=C2CCC(OC2=C(C1C)C)(C)COC1=CC=C(C=C1)CC(C(=O)OCC)Cl)C
|
|
Name
|
|
|
Quantity
|
1.8 g
|
|
Type
|
reactant
|
|
Smiles
|
NC(=S)N
|
|
Name
|
|
|
Quantity
|
11 mL
|
|
Type
|
reactant
|
|
Smiles
|
S1(=O)(=O)CCCC1
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
Cl
|
Step Three
|
Name
|
|
|
Quantity
|
100 mL
|
|
Type
|
solvent
|
|
Smiles
|
COCCO
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
120 °C
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
were then added to the reaction mixture
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
after which it was heated
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
under reflux for 12 hours
|
|
Duration
|
12 h
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The product was then purified
|
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
|
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. |
