5-Ethyl-2-pyridineethanol Tosylate
カタログ番号 B139052
分子量: 305.4 g/mol
InChIキー: XOKOJAMQAAPMRF-UHFFFAOYSA-N
注意: 研究専用です。人間または獣医用ではありません。
Patent
US07009057B2
Procedure details
0.5 g of 5-(4-hydroxybenzyl)-1,3-thiazolidine-2,4-dione is dissolved in ethanol (7 ml) with KOH (0.25 g) and mixed at room temperature for 2 hours. To the obtained salt 2-(5-ethyl-2-pyridyl)ethyl tosylate is added and the reaction mixture is refluxed for 5 hours. After cooling the precipitated salt is filtered off, pH is adjusted and the solvent is evaporated. The semi-solid residue is mixed in water and the solid portion of 5-[[4-[2-(5-ethyl-2-pyridyl) ethoxy]phenyl]methyl]-2.4-thiazolidinedione (0.18 g) is filtered off and recrystallized from the mixture DMF-water.
Identifiers
|
REACTION_CXSMILES
|
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[OH-].[K+].S(C1C=CC(C)=CC=1)(O[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH3:31])=[CH:26][N:25]=1)(=O)=O>C(O)C>[CH2:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH2:22][O:1][C:2]2[CH:15]=[CH:14][C:5]([CH2:6][CH:7]3[S:11][C:10](=[O:12])[NH:9][C:8]3=[O:13])=[CH:4][CH:3]=2)=[N:25][CH:26]=1)[CH3:31] |f:1.2|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0.5 g
|
|
Type
|
reactant
|
|
Smiles
|
OC1=CC=C(CC2C(NC(S2)=O)=O)C=C1
|
|
Name
|
|
|
Quantity
|
0.25 g
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[K+]
|
|
Name
|
|
|
Quantity
|
7 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)O
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
S(=O)(=O)(OCCC1=NC=C(C=C1)CC)C1=CC=C(C)C=C1
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
mixed at room temperature for 2 hours
|
|
Duration
|
2 h
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
the reaction mixture is refluxed for 5 hours
|
|
Duration
|
5 h
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
After cooling the precipitated salt
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
is filtered off
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the solvent is evaporated
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
The semi-solid residue is mixed in water
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the solid portion of 5-[[4-[2-(5-ethyl-2-pyridyl) ethoxy]phenyl]methyl]-2.4-thiazolidinedione (0.18 g) is filtered off
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
recrystallized from the mixture DMF-water
|
Outcomes
Product
|
Name
|
|
|
Type
|
|
|
Smiles
|
C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C1)CC1C(NC(S1)=O)=O
|
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
US07009057B2
Procedure details
0.5 g of 5-(4-hydroxybenzyl)-1,3-thiazolidine-2,4-dione is dissolved in ethanol (7 ml) with KOH (0.25 g) and mixed at room temperature for 2 hours. To the obtained salt 2-(5-ethyl-2-pyridyl)ethyl tosylate is added and the reaction mixture is refluxed for 5 hours. After cooling the precipitated salt is filtered off, pH is adjusted and the solvent is evaporated. The semi-solid residue is mixed in water and the solid portion of 5-[[4-[2-(5-ethyl-2-pyridyl) ethoxy]phenyl]methyl]-2.4-thiazolidinedione (0.18 g) is filtered off and recrystallized from the mixture DMF-water.
Identifiers
|
REACTION_CXSMILES
|
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[OH-].[K+].S(C1C=CC(C)=CC=1)(O[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH3:31])=[CH:26][N:25]=1)(=O)=O>C(O)C>[CH2:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH2:22][O:1][C:2]2[CH:15]=[CH:14][C:5]([CH2:6][CH:7]3[S:11][C:10](=[O:12])[NH:9][C:8]3=[O:13])=[CH:4][CH:3]=2)=[N:25][CH:26]=1)[CH3:31] |f:1.2|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0.5 g
|
|
Type
|
reactant
|
|
Smiles
|
OC1=CC=C(CC2C(NC(S2)=O)=O)C=C1
|
|
Name
|
|
|
Quantity
|
0.25 g
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[K+]
|
|
Name
|
|
|
Quantity
|
7 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)O
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
S(=O)(=O)(OCCC1=NC=C(C=C1)CC)C1=CC=C(C)C=C1
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
mixed at room temperature for 2 hours
|
|
Duration
|
2 h
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
the reaction mixture is refluxed for 5 hours
|
|
Duration
|
5 h
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
After cooling the precipitated salt
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
is filtered off
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the solvent is evaporated
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
The semi-solid residue is mixed in water
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the solid portion of 5-[[4-[2-(5-ethyl-2-pyridyl) ethoxy]phenyl]methyl]-2.4-thiazolidinedione (0.18 g) is filtered off
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
recrystallized from the mixture DMF-water
|
Outcomes
Product
|
Name
|
|
|
Type
|
|
|
Smiles
|
C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=C1)CC1C(NC(S1)=O)=O
|
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. |
