Pyridinium bromide
カタログ番号 B8452845
分子量: 160.01 g/mol
InChIキー: BBFCIBZLAVOLCF-UHFFFAOYSA-N
注意: 研究専用です。人間または獣医用ではありません。
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
|
|
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
|
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
|
|
Smiles
|
O
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Step Two
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Name
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Quantity
|
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.
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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. |
