Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate
カタログ番号 B031883
分子量: 319.31 g/mol
InChIキー: RIGKLAOKQFKWNN-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
US04661485
Procedure details
Methyl 3-aminocrotonate (72.2 g; 0.627M) and 2-chlorobenzaldehyde (88.1 g; 0.627M) were added to a solution of ethyl 4-(2-phthalimidoethoxy)acetoacetate (200 g; 0.627M) in isopropanol (1 liter) and the mixture was heated under reflux for 20 hours. The isopropanol was evaporated under reduced pressure and replaced by acetic acid (1 liter). After granulation at 10° the solid was collected and slurried in methanol (300 ml). The solid was collected by filtration and dried in vacuo at 50° to afford the title compound, yield 84.4 g, m.p. 146°-147°.
Identifiers
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REACTION_CXSMILES
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[NH2:1]/[C:2](/[CH3:8])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5].[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O.[C:18]1(=[O:40])[N:22]([CH2:23][CH2:24][O:25][CH2:26][C:27](=O)[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:21](=[O:35])[C:20]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:19]12>C(O)(C)C>[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([CH3:8])[NH:1][C:27]([CH2:26][O:25][CH2:24][CH2:23][N:22]2[C:21](=[O:35])[C:20]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:19]3[C:18]2=[O:40])=[C:28]1[C:29]([O:31][CH2:32][CH3:33])=[O:30]
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Inputs
Step One
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Name
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Quantity
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72.2 g
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Type
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reactant
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Smiles
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N\C(=C/C(=O)OC)\C
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Name
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Quantity
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88.1 g
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Type
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reactant
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Smiles
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ClC1=C(C=O)C=CC=C1
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Name
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Quantity
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200 g
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Type
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reactant
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Smiles
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C1(C=2C(C(N1CCOCC(CC(=O)OCC)=O)=O)=CC=CC2)=O
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Name
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Quantity
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1 L
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Type
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solvent
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Smiles
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C(C)(C)O
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Conditions
Other
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Conditions are dynamic
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1
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Details
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See reaction.notes.procedure_details.
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Workups
TEMPERATURE
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Type
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TEMPERATURE
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Details
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the mixture was heated
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TEMPERATURE
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Type
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TEMPERATURE
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Details
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under reflux for 20 hours
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Duration
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20 h
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CUSTOM
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Type
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CUSTOM
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Details
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The isopropanol was evaporated under reduced pressure
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CUSTOM
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Type
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CUSTOM
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Details
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After granulation at 10° the solid was collected
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FILTRATION
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Type
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FILTRATION
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Details
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The solid was collected by filtration
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CUSTOM
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Type
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CUSTOM
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Details
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dried in vacuo at 50°
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Outcomes
Product
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Name
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Type
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product
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Smiles
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ClC1=C(C=CC=C1)C1C(=C(NC(=C1C(=O)OC)C)COCCN1C(C=2C(C1=O)=CC=CC2)=O)C(=O)OCC
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Source
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Source
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Open Reaction Database (ORD) |
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Description
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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. |
