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molecular formula C9H7Cl2N5 B1674446 Lamotrigine CAS No. 84057-84-1

Lamotrigine

Cat. No. B1674446
M. Wt: 256.09 g/mol
InChI Key: PYZRQGJRPPTADH-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US04649139

Procedure details

A solution of 2,3-dichlorobenzoyl cyanide (32 g, 0.16M) in dimethylsulphoxide (80 ml) was added dropwise to a stirred suspension of aminoguanidine bicarbonate (81.67 g. 0.6M) which had been treated with 8N aqueous nitric acid (400 ml) at a temperature of ca 25° C. The mixture was stirred for 3 hours, then left to stand at room temperature for 7 days. The cooled mixture was stirred and basified with 0.880 aqueous ammonia (400 ml) at 20° C., then stirred with ice cooling for 30 minutes. The resulting solid was separated by filtration, washed thoroughly with water and finally dried in vacuo. The above solid was added to a 10% w/v solution of potassium hydroxide pellets in methanol (400 ml) and the solution heated to reflux for 11/2 hours. When cool the solution was evaporated down in vacuo, treated with ice water (800 ml) then stirred for 30 minutes and filtered. The residue was dried and recrystallised from isopropanol to give 3,5-diamino-(2,3-dichlorophenyl)-1,2,4-triazine Yield 6.8 g (15.6%), m.p. 216°-218° C. (uncorrected).
Quantity
32 g
Type
reactant
Reaction Step One
Quantity
81.67 g
Type
reactant
Reaction Step One
Quantity
80 mL
Type
solvent
Reaction Step One
Quantity
400 mL
Type
reactant
Reaction Step Two
Quantity
400 mL
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([C:6]#[N:7])=O.C(=O)(O)O.[NH2:17][NH:18][C:19]([NH2:21])=[NH:20].[N+]([O-])(O)=O.N>CS(C)=O>[NH2:20][C:19]1[N:18]=[N:17][C:4]([C:3]2[CH:8]=[CH:9][CH:10]=[C:11]([Cl:12])[C:2]=2[Cl:1])=[C:6]([NH2:7])[N:21]=1 |f:1.2|

Inputs

Step One
Name
Quantity
32 g
Type
reactant
Smiles
ClC1=C(C(=O)C#N)C=CC=C1Cl
Name
Quantity
81.67 g
Type
reactant
Smiles
C(O)(O)=O.NNC(=N)N
Name
Quantity
80 mL
Type
solvent
Smiles
CS(=O)C
Step Two
Name
Quantity
400 mL
Type
reactant
Smiles
[N+](=O)(O)[O-]
Step Three
Name
Quantity
400 mL
Type
reactant
Smiles
N

Conditions

Stirring
Type
CUSTOM
Details
The mixture was stirred for 3 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

WAIT
Type
WAIT
Details
left
WAIT
Type
WAIT
Details
to stand at room temperature for 7 days
Duration
7 d
STIRRING
Type
STIRRING
Details
The cooled mixture was stirred
STIRRING
Type
STIRRING
Details
stirred with ice cooling for 30 minutes
Duration
30 min
CUSTOM
Type
CUSTOM
Details
The resulting solid was separated by filtration
WASH
Type
WASH
Details
washed thoroughly with water
CUSTOM
Type
CUSTOM
Details
finally dried in vacuo
ADDITION
Type
ADDITION
Details
The above solid was added to a 10% w/v solution of potassium hydroxide pellets in methanol (400 ml)
TEMPERATURE
Type
TEMPERATURE
Details
the solution heated
TEMPERATURE
Type
TEMPERATURE
Details
to reflux for 11/2 hours
Duration
2 h
TEMPERATURE
Type
TEMPERATURE
Details
When cool the solution
CUSTOM
Type
CUSTOM
Details
was evaporated down in vacuo
ADDITION
Type
ADDITION
Details
treated with ice water (800 ml)
STIRRING
Type
STIRRING
Details
then stirred for 30 minutes
Duration
30 min
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The residue was dried
CUSTOM
Type
CUSTOM
Details
recrystallised from isopropanol

Outcomes

Product
Details
Reaction Time
3 h
Name
Type
product
Smiles
NC=1N=NC(=C(N1)N)C1=C(C(=CC=C1)Cl)Cl
Measurements
Type Value Analysis
AMOUNT: MASS 6.8 g
YIELD: PERCENTYIELD 15.6%
YIELD: CALCULATEDPERCENTYIELD 16.6%

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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