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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
US07015322B1

Procedure details

30 g iminostilbene are heated to 60° C. in 360 ml acetic acid and 50 ml ethanol, and 20 g 98% sodium cyanate is added within 1.5 hours at this temperature. After a short heating to 80° C., the mixture is further stirred at 60° C., and then cooled to 15° C., sucked off, washed with 20 l acetic acid and dried to yield 29.4 g (80.3% of theoretical) of carbamazepine, having a melting point of 189° C. to 192° C.
Quantity
30 g
Type
reactant
Reaction Step One
Quantity
360 mL
Type
solvent
Reaction Step One
Name
sodium cyanate
Quantity
20 g
Type
reactant
Reaction Step Two
Quantity
50 mL
Type
solvent
Reaction Step Two
Yield
80.3%

Identifiers

REACTION_CXSMILES
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.[O-:16][C:17]#[N:18].[Na+]>C(O)(=O)C.C(O)C>[CH:1]1[CH:2]=[CH:3][C:4]2[N:15]([C:17]([NH2:18])=[O:16])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1 |f:1.2|

Inputs

Step One
Name
Quantity
30 g
Type
reactant
Smiles
C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2
Name
Quantity
360 mL
Type
solvent
Smiles
C(C)(=O)O
Step Two
Name
sodium cyanate
Quantity
20 g
Type
reactant
Smiles
[O-]C#N.[Na+]
Name
Quantity
50 mL
Type
solvent
Smiles
C(C)O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
80 °C
Stirring
Type
CUSTOM
Details
the mixture is further stirred at 60° C.
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
cooled to 15° C.
WASH
Type
WASH
Details
washed with 20 l acetic acid
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2C(=O)N
Measurements
Type Value Analysis
AMOUNT: MASS 29.4 g
YIELD: PERCENTYIELD 80.3%
YIELD: CALCULATEDPERCENTYIELD 80.2%

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
US07015322B1

Procedure details

30 g iminostilbene are heated to 60° C. in 360 ml acetic acid and 50 ml ethanol, and 20 g 98% sodium cyanate is added within 1.5 hours at this temperature. After a short heating to 80° C., the mixture is further stirred at 60° C., and then cooled to 15° C., sucked off, washed with 20 l acetic acid and dried to yield 29.4 g (80.3% of theoretical) of carbamazepine, having a melting point of 189° C. to 192° C.
Quantity
30 g
Type
reactant
Reaction Step One
Quantity
360 mL
Type
solvent
Reaction Step One
Name
sodium cyanate
Quantity
20 g
Type
reactant
Reaction Step Two
Quantity
50 mL
Type
solvent
Reaction Step Two
Yield
80.3%

Identifiers

REACTION_CXSMILES
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.[O-:16][C:17]#[N:18].[Na+]>C(O)(=O)C.C(O)C>[CH:1]1[CH:2]=[CH:3][C:4]2[N:15]([C:17]([NH2:18])=[O:16])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1 |f:1.2|

Inputs

Step One
Name
Quantity
30 g
Type
reactant
Smiles
C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2
Name
Quantity
360 mL
Type
solvent
Smiles
C(C)(=O)O
Step Two
Name
sodium cyanate
Quantity
20 g
Type
reactant
Smiles
[O-]C#N.[Na+]
Name
Quantity
50 mL
Type
solvent
Smiles
C(C)O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
80 °C
Stirring
Type
CUSTOM
Details
the mixture is further stirred at 60° C.
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
cooled to 15° C.
WASH
Type
WASH
Details
washed with 20 l acetic acid
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2C(=O)N
Measurements
Type Value Analysis
AMOUNT: MASS 29.4 g
YIELD: PERCENTYIELD 80.3%
YIELD: CALCULATEDPERCENTYIELD 80.2%

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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