Oxcarbazepine
货号 B1677851
分子量: 252.27 g/mol
InChI 键: CTRLABGOLIVAIY-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US06670472B2
Procedure details
A mixture of 100 gms of 10-methoxyiminostilbene in 2000 mL of toluene containing 274 gms of benzoic acid and 370 gms of sodium cyanate were heated to reflux temperature under stirring and maintained for 12 hours. The reaction mixture was then cooled to room temperature and filtered. The clear toluene filtrate was 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 75-90° 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 46 gms of pure oxcarbazepine. Purity was determined by HPLC to be 99.45%.
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.C(O)(=O)C1C=CC=CC=1.[O-:27][C:28]#[N:29].[Na+]>C1(C)C=CC=CC=1>[CH:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:28]([NH2:29])=[O:27])[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
|
COC1=CC2=CC=CC=C2NC3=CC=CC=C31
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C(C1=CC=CC=C1)(=O)O
|
|
Name
|
sodium cyanate
|
|
Quantity
|
370 g
|
|
Type
|
reactant
|
|
Smiles
|
[O-]C#N.[Na+]
|
|
Name
|
|
|
Quantity
|
2000 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1(=CC=CC=C1)C
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
under stirring
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
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
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
maintained for 12 hours
|
|
Duration
|
12 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
The clear toluene filtrate was 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 75-90° 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 | 46 g | |
| YIELD: CALCULATEDPERCENTYIELD | 40.7% |
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. |
