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molecular formula C15H12N2O2 B1677851 Oxcarbazepine CAS No. 28721-07-5

Oxcarbazepine

Cat. No. B1677851
M. Wt: 252.27 g/mol
InChI Key: CTRLABGOLIVAIY-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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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.
Quantity
100 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
sodium cyanate
Quantity
370 g
Type
reactant
Reaction Step One
Quantity
1000 mL
Type
solvent
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|

Inputs

Step One
Name
Quantity
100 g
Type
reactant
Smiles
COC1=CC2=CC=CC=C2NC3=CC=CC=C31
Name
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

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
were heated
TEMPERATURE
Type
TEMPERATURE
Details
to reflux
TEMPERATURE
Type
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.
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