Pyridinium bromide
Numéro de catalogue B8452845
Poids moléculaire: 160.01 g/mol
Clé InChI: BBFCIBZLAVOLCF-UHFFFAOYSA-N
Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.
Patent
US07091339B2
Procedure details
The carbamoylation reaction was performed as in Example 1. After about 7–8 hours of stirring the carbamoylation reaction mixture (containing pyridinium bromide, 10-methoxy-5H-dibenz[b,f]azepine, water, toluene, and NaOCN) at room temperature (22° C.), the mixture was heated to 55–60° C., and 500 ml of 10% HCl was added drop-wise and carefully. The reaction mixture was warmed to reflux (89° C.) for 3–4 hours, and then worked up and purified as in Example 1. 32.8 g (58% yield) of crude oxcarbazepine was obtained. The crude afforded 24.9 g (44% overall yield) of pure oxcarbazepine.
Name
NaOCN
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Yield
58%
Identifiers
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REACTION_CXSMILES
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[Br-].[NH+]1C=CC=CC=1.C[O:9][C:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][C:13]2[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=2[CH:11]=1.[O:25]([C:27]#[N:28])[Na].Cl>C1(C)C=CC=CC=1.O>[CH:23]1[CH:22]=[CH:21][C:13]2[N:14]([C:27]([NH2:28])=[O:25])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:10](=[O:9])[CH2:11][C:12]=2[CH:24]=1 |f:0.1|
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Inputs
Step One
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Name
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|
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Quantity
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0 (± 1) mol
|
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Type
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reactant
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Smiles
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[Br-].[NH+]1=CC=CC=C1
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Name
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Quantity
|
0 (± 1) mol
|
|
Type
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reactant
|
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Smiles
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COC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2
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Name
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NaOCN
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Quantity
|
0 (± 1) mol
|
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Type
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reactant
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Smiles
|
O([Na])C#N
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Name
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Quantity
|
0 (± 1) mol
|
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Type
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solvent
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Smiles
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C1(=CC=CC=C1)C
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Name
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Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
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Smiles
|
O
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Step Two
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Name
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Quantity
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500 mL
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Type
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reactant
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Smiles
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Cl
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Conditions
Temperature
|
Control Type
|
UNSPECIFIED
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Setpoint
|
89 °C
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Stirring
|
Type
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CUSTOM
|
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Details
|
After about 7–8 hours of stirring
|
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Rate
|
UNSPECIFIED
|
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RPM
|
0
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Other
|
Conditions are dynamic
|
1
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Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
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Details
|
The carbamoylation reaction
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TEMPERATURE
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Type
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TEMPERATURE
|
|
Details
|
the mixture was heated to 55–60° C.
|
TEMPERATURE
|
Type
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TEMPERATURE
|
|
Details
|
The reaction mixture was warmed
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CUSTOM
|
Type
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CUSTOM
|
|
Details
|
purified as in Example 1
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Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C=1C=CC2=C(C1)CC(=O)C=3C=CC=CC3N2C(=O)N
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Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 32.8 g | |
| YIELD: PERCENTYIELD | 58% |
Source
|
Source
|
Open Reaction Database (ORD) |
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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. |
