Oxcarbazepine
Número de catálogo B1677851
Peso molecular: 252.27 g/mol
Clave InChI: CTRLABGOLIVAIY-UHFFFAOYSA-N
Atención: Solo para uso de investigación. No para uso humano o veterinario.
Patent
US06670472B2
Procedure details
A mixture of 100 gms of 10-methoxyiminostilbene in 1000 mL of toluene containing 430 gms of 2,4-dichlorobenzoic acid and 370 gms of sodium cyanate were heated to reflux and refluxed for 6 hours. The reaction mixture was then cooled to room temperature and filtered. The clear toluene filtrate was then washed with 5% sodium carbonate solution followed by water. The toluene layer was then added to 1000 mL of 2N hydrochloric acid and the mixture was heated at 75-80° C. for a period of 2 hours under good agitation. It was then cooled to 0-5° C., maintained for 2 hours and the product oxcarbazepine was separated by filtration. This was then purified once in a dichloromethane:methanol mixture to furnish 40 gms of pure oxcarbazepine.
Name
sodium cyanate
Quantity
370 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
C[O:2][C:3]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.ClC1C=C(Cl)C=CC=1C(O)=O.[O-:29][C:30]#[N:31].[Na+]>C1(C)C=CC=CC=1>[CH:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:30]([NH2:31])=[O:29])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:3](=[O:2])[CH2:4][C:5]=2[CH:6]=1 |f:2.3|
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Inputs
Step One
|
Name
|
|
|
Quantity
|
100 g
|
|
Type
|
reactant
|
|
Smiles
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COC1=CC2=CC=CC=C2NC3=CC=CC=C31
|
|
Name
|
|
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Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
ClC1=C(C(=O)O)C=CC(=C1)Cl
|
|
Name
|
sodium cyanate
|
|
Quantity
|
370 g
|
|
Type
|
reactant
|
|
Smiles
|
[O-]C#N.[Na+]
|
|
Name
|
|
|
Quantity
|
1000 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1(=CC=CC=C1)C
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Conditions
Temperature
|
Control Type
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AMBIENT
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
were heated
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TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to reflux
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TEMPERATURE
|
Type
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TEMPERATURE
|
|
Details
|
refluxed for 6 hours
|
|
Duration
|
6 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
The clear toluene filtrate was then washed with 5% sodium carbonate solution
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
The toluene layer was then added to 1000 mL of 2N hydrochloric acid
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
the mixture was heated at 75-80° C. for a period of 2 hours under good agitation
|
|
Duration
|
2 h
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
It was then cooled to 0-5° C.
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
maintained for 2 hours
|
|
Duration
|
2 h
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the product oxcarbazepine was separated by filtration
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
This was then purified once in a dichloromethane
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C=1C=CC2=C(C1)CC(=O)C=3C=CC=CC3N2C(=O)N
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 40 g | |
| YIELD: CALCULATEDPERCENTYIELD | 35.4% |
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. |
