Welcome to the BenchChem Online Store!
molecular formula C5H6BrN B8452845 Pyridinium bromide

Pyridinium bromide

Cat. No. B8452845
M. Wt: 160.01 g/mol
InChI Key: BBFCIBZLAVOLCF-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
  • Click on QUICK INQUIRY to receive a quote from our team of experts.
  • With the quality product at a COMPETITIVE price, you can focus more on your research.
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.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
NaOCN
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Name
Quantity
500 mL
Type
reactant
Reaction Step Two
Yield
58%

Identifiers

REACTION_CXSMILES
[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|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[Br-].[NH+]1=CC=CC=C1
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
COC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2
Name
NaOCN
Quantity
0 (± 1) mol
Type
reactant
Smiles
O([Na])C#N
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C1(=CC=CC=C1)C
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O
Step Two
Name
Quantity
500 mL
Type
reactant
Smiles
Cl

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
89 °C
Stirring
Type
CUSTOM
Details
After about 7–8 hours of stirring
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
The carbamoylation reaction
TEMPERATURE
Type
TEMPERATURE
Details
the mixture was heated to 55–60° C.
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was warmed
CUSTOM
Type
CUSTOM
Details
purified as in Example 1

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC2=C(C1)CC(=O)C=3C=CC=CC3N2C(=O)N
Measurements
Type Value Analysis
AMOUNT: MASS 32.8 g
YIELD: PERCENTYIELD 58%

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.
© Copyright 2024 BenchChem. All Rights Reserved.