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molecular formula C15H12N2O B1668303 Carbamazepine CAS No. 298-46-4

Carbamazepine

Cat. No. B1668303
M. Wt: 236.27 g/mol
InChI Key: FFGPTBGBLSHEPO-UHFFFAOYSA-N
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Patent
US06245908B1

Procedure details

To a suspension of urea (80 g, 1.333 mols) in acetic acid (100 ml), iminostilbene hydrochloride (20.5 g, 0.089 mols) was added under stirring at 25-30° C. The resulting reaction mixture was worked up according to the method of Example 1 to produce carbamazepine, which was identical to the product of Example 1.
Name
Quantity
80 g
Type
reactant
Reaction Step One
Name
iminostilbene hydrochloride
Quantity
20.5 g
Type
reactant
Reaction Step One
Quantity
100 mL
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[NH2:1][C:2]([NH2:4])=[O:3].Cl.N=[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]1[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(=O)C>[CH:10]1[CH:11]=[CH:12][C:7]2[N:1]([C:2]([NH2:4])=[O:3])[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH:14]=[CH:13][C:8]=2[CH:9]=1 |f:1.2|

Inputs

Step One
Name
Quantity
80 g
Type
reactant
Smiles
NC(=O)N
Name
iminostilbene hydrochloride
Quantity
20.5 g
Type
reactant
Smiles
Cl.N=C1C(C=CC=C1)C=CC1=CC=CC=C1
Name
Quantity
100 mL
Type
solvent
Smiles
C(C)(=O)O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
27.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
under stirring at 25-30° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added
CUSTOM
Type
CUSTOM
Details
The resulting reaction mixture

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2C(=O)N

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.
Patent
US06245908B1

Procedure details

To a suspension of urea (80 g, 1.333 mols) in acetic acid (100 ml), iminostilbene hydrochloride (20.5 g, 0.089 mols) was added under stirring at 25-30° C. The resulting reaction mixture was worked up according to the method of Example 1 to produce carbamazepine, which was identical to the product of Example 1.
Name
Quantity
80 g
Type
reactant
Reaction Step One
Name
iminostilbene hydrochloride
Quantity
20.5 g
Type
reactant
Reaction Step One
Quantity
100 mL
Type
solvent
Reaction Step One

Identifiers

REACTION_CXSMILES
[NH2:1][C:2]([NH2:4])=[O:3].Cl.N=[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]1[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(=O)C>[CH:10]1[CH:11]=[CH:12][C:7]2[N:1]([C:2]([NH2:4])=[O:3])[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH:14]=[CH:13][C:8]=2[CH:9]=1 |f:1.2|

Inputs

Step One
Name
Quantity
80 g
Type
reactant
Smiles
NC(=O)N
Name
iminostilbene hydrochloride
Quantity
20.5 g
Type
reactant
Smiles
Cl.N=C1C(C=CC=C1)C=CC1=CC=CC=C1
Name
Quantity
100 mL
Type
solvent
Smiles
C(C)(=O)O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
27.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
under stirring at 25-30° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added
CUSTOM
Type
CUSTOM
Details
The resulting reaction mixture

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2C(=O)N

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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