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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

ethyl (2E)-2-[(2-chlorophenyl)methylidene]-4-[2-(1,3-dioxoisoindol-2-yl)ethoxy]-3-oxobutanoate

Cat. No. B1141314
M. Wt: 441.86
InChI Key:
Attention: For research use only. Not for human or veterinary use.
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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.

Identifiers

REACTION_CXSMILES
[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]

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
Name
Quantity
50 g
Type
reactant
Smiles
COC(\C=C(\C)/N)=O

Conditions

Temperature
Control Type
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
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

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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