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molecular formula C16H14N2O2 B195698 10-Methoxycarbamazepine CAS No. 28721-09-7

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.
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Patent
US07112673B2

Procedure details

Acetic acid (150 mL) is added dropwise to a stirred mixture of 10-methoxy-5H-dibenzo[b,f]azepine (25.0 g, 112 mmol) and NaOCN (9.25 g, 142 mmol) under a nitrogen atmosphere at room temperature. After stirring for 7 hours the resulting yellow suspension of the title compound (>95% area of the compound by HPLC) is used for synthesis of 10-oxo-10,11-dihydro-dibenzo[b,f]azepine-S-carboxylic acid amide. The title compound can be isolated by adding 1N NaOH to a pH of ≧8 followed by extraction with toluene. Drying of the combined organic layers and concentration in vacuo yields the title compound as a light yellow solid (yield≧75%).
Quantity
25 g
Type
reactant
Reaction Step One
Name
NaOCN
Quantity
9.25 g
Type
reactant
Reaction Step One
Quantity
150 mL
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[CH3:1][O:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1.[O:18]([C:20]#[N:21])[Na]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:20]([NH2:21])=[O:18])[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1

Inputs

Step One
Name
Quantity
25 g
Type
reactant
Smiles
COC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2
Name
NaOCN
Quantity
9.25 g
Type
reactant
Smiles
O([Na])C#N
Name
Quantity
150 mL
Type
solvent
Smiles
C(C)(=O)O

Conditions

Stirring
Type
CUSTOM
Details
After stirring for 7 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Outcomes

Product
Details
Reaction Time
7 h
Name
Type
product
Smiles
COC1=CC2=C(N(C3=C1C=CC=C3)C(=O)N)C=CC=C2

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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