10-Methoxycarbamazepine
Cat. No. B195698
M. Wt: 266.29 g/mol
InChI Key: PIZOFBKQWNPKDK-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
Patent
US08530647B2
Procedure details
100 g of 10-methoxycarbamazepine in 1000 ml water and 69.24 g of oxalic acid solution were heated to 90° C. and maintained for about 17 hrs. After completion of the reaction the reaction mixture was cooled to room temperature (RT). The resulting reaction mass was filtered and washed with 1000 ml of DM water. The wet material obtained was charged with isopropyl alcohol and DM water. The obtained reaction mixture was heated to reflux for about 2 h. The reaction mixture was cooled to 15-25° C., filtered and washed with 100 ml of IPA-water mixture. The resulting compound is dried at 60° C. for 6 h to produce 90 g of Oxcarbazepine.
Name
Identifiers
|
REACTION_CXSMILES
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C[O:2][C:3]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]([NH2:20])=[O:19])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.C(O)(=O)C(O)=O.C(O)(C)C>O>[CH:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:18]([NH2:20])=[O:19])[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
|
Inputs
Step One
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Name
|
|
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Quantity
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100 g
|
|
Type
|
reactant
|
|
Smiles
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COC1=CC2=CC=CC=C2N(C3=CC=CC=C31)C(=O)N
|
|
Name
|
|
|
Quantity
|
69.24 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C(=O)O)(=O)O
|
|
Name
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|
|
Quantity
|
1000 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C(C)(C)O
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
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AMBIENT
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Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
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Workups
TEMPERATURE
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Type
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TEMPERATURE
|
|
Details
|
maintained for about 17 hrs
|
|
Duration
|
17 h
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CUSTOM
|
Type
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CUSTOM
|
|
Details
|
After completion of the reaction the reaction mixture
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CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The resulting reaction mass
|
FILTRATION
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Type
|
FILTRATION
|
|
Details
|
was filtered
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WASH
|
Type
|
WASH
|
|
Details
|
washed with 1000 ml of DM water
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The wet material obtained
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The obtained reaction mixture
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
was heated
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to reflux for about 2 h
|
|
Duration
|
2 h
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
The reaction mixture was cooled to 15-25° C.
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
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WASH
|
Type
|
WASH
|
|
Details
|
washed with 100 ml of IPA-water mixture
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The resulting compound is dried at 60° C. for 6 h
|
|
Duration
|
6 h
|
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 | 90 g | |
| YIELD: CALCULATEDPERCENTYIELD | 95% |
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. |
