Carbamazepine
Katalognummer B1668303
:
298-46-4
Molekulargewicht: 236.27 g/mol
InChI-Schlüssel: FFGPTBGBLSHEPO-UHFFFAOYSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
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.
Name
sodium cyanate
Quantity
20 g
Type
reactant
Reaction Step Two
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.
Name
sodium cyanate
Quantity
20 g
Type
reactant
Reaction Step Two
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. |
