![molecular formula C₂₃H₂₀ClNO₆ B1141314 ethyl (2E)-2-[(2-chlorophenyl)methylidene]-4-[2-(1,3-dioxoisoindol-2-yl)ethoxy]-3-oxobutanoate CAS No. 400024-08-0](/img/structure/B1141314.png)
Patent
US06858738B2
Procedure details
350 g of crude ethyl 2-(o-chlorobenzylidene)-4-(2-phthalimidoethoxy) acetoacetate from Example 1 was dissolved in 540 ml of 2-propanol at 80° C. 50 g of methyl-3-aminocrotonate was added and the mixture was heated at the same temperature for 16 hours. The mixture was evaporated to dryness. The residue was dissolved in 540 ml of glacial acetic acid at 80° C. The mixture was cooled to 15° C. and stirred at the same temperature for 20 hours. The formed solid was filtered off and washed with 280 ml of glacial acetic acid. The solid was suspended in 225 ml of methanol and agitated for 30 minutes. The solid was filtered off, washed with 75 ml of methanol and dried.
Quantity
350 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
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[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH:4]=[C:5]([C:11]([CH2:13][O:14][CH2:15][CH2:16][N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:32][O:33][C:34](=[O:39])/[CH:35]=[C:36](\[NH2:38])/[CH3:37]>CC(O)C>[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH:4]1[C:35]([C:34]([O:33][CH3:32])=[O:39])=[C:36]([CH3:37])[NH:38][C:11]([CH2:13][O:14][CH2:15][CH2:16][N:17]2[C:21](=[O:22])[C:20]3[C:19](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]2=[O:27])=[C:5]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]
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Inputs
Step One
|
Name
|
|
|
Quantity
|
350 g
|
|
Type
|
reactant
|
|
Smiles
|
ClC1=C(C=C(C(=O)OCC)C(=O)COCCN2C(C=3C(C2=O)=CC=CC3)=O)C=CC=C1
|
|
Name
|
|
|
Quantity
|
540 mL
|
|
Type
|
solvent
|
|
Smiles
|
CC(C)O
|
Step Two
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Name
|
|
|
Quantity
|
50 g
|
|
Type
|
reactant
|
|
Smiles
|
COC(\C=C(\C)/N)=O
|
Conditions
Temperature
|
Control Type
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UNSPECIFIED
|
|
Setpoint
|
15 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
stirred at the same temperature for 20 hours
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
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Type
|
TEMPERATURE
|
|
Details
|
the mixture was heated at the same temperature for 16 hours
|
|
Duration
|
16 h
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The mixture was evaporated to dryness
|
DISSOLUTION
|
Type
|
DISSOLUTION
|
|
Details
|
The residue was dissolved in 540 ml of glacial acetic acid at 80° C
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The formed solid was filtered off
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with 280 ml of glacial acetic acid
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
agitated for 30 minutes
|
|
Duration
|
30 min
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The solid was filtered off
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with 75 ml of methanol
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
Outcomes
Product
Details
Reaction Time |
20 h |
|
Name
|
|
|
Type
|
|
|
Smiles
|
ClC1=C(C=CC=C1)C1C(=C(NC(=C1C(=O)OC)C)COCCN1C(C2=CC=CC=C2C1=O)=O)C(=O)OCC
|
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. |
