Tetramisole
Katalognummer B1196661
Molekulargewicht: 204.29 g/mol
InChI-Schlüssel: HLFSDGLLUJUHTE-UHFFFAOYSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
Patent
US04672126
Procedure details
A suspension of 31.73 g of L-N-[(4-methoxyphenyl)sulfonyl-glutamic acid (0.1 mol) in 400 ml of 2-propanone and 20 ml of water was stirred and heated till all solid entered solution. Then there were added 20.43 g of tetramisole. The whole was stirred and heated to reflux and additionally stirred at reflux for 10 minutes. The mixture was further stirred for 4 hours while the temperature was allowed to reach room temperature. The precipitate was filtered off, washed with 100 ml of 2-propanone and 5 ml of water and dried under vacuo at 50° C., yielding 25.55 g of levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) (yield 98%) αD20 =-62.4° (c5. 1N HCl); mp. 127.3°-129° C.
Identifiers
|
REACTION_CXSMILES
|
COC1C=CC(S(N[C@H](C(O)=O)CCC(O)=O)(=O)=O)=CC=1.[CH:22]1[CH:23]=[CH:24][C:25]([CH:28]2[N:35]=[C:34]3[N:30]([CH2:31][CH2:32][S:33]3)[CH2:29]2)=[CH:26][CH:27]=1>CC(=O)C.O>[CH:22]1[CH:27]=[CH:26][C:25]([C@@H:28]2[N:35]=[C:34]3[N:30]([CH2:31][CH2:32][S:33]3)[CH2:29]2)=[CH:24][CH:23]=1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0.1 mol
|
|
Type
|
reactant
|
|
Smiles
|
COC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CCC(=O)O)C(=O)O
|
|
Name
|
|
|
Quantity
|
400 mL
|
|
Type
|
solvent
|
|
Smiles
|
CC(C)=O
|
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Two
|
Name
|
|
|
Quantity
|
20.43 g
|
|
Type
|
reactant
|
|
Smiles
|
C=1C=CC(=CC1)C2CN3CCSC3=N2
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
was stirred
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
heated till all solid
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
The whole was stirred
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
heated
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to reflux
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
additionally stirred
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
at reflux for 10 minutes
|
|
Duration
|
10 min
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
The mixture was further stirred for 4 hours while the temperature
|
|
Duration
|
4 h
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to reach room temperature
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The precipitate was filtered off
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with 100 ml of 2-propanone and 5 ml of water
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried under vacuo at 50° C.
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C=1C=CC(=CC1)[C@H]2CN3CCSC3=N2
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 25.55 g | |
| YIELD: CALCULATEDPERCENTYIELD | 125.1% |
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
US04672126
Procedure details
A suspension of 31.73 g of L-N-[(4-methoxyphenyl)sulfonyl-glutamic acid (0.1 mol) in 400 ml of 2-propanone and 20 ml of water was stirred and heated till all solid entered solution. Then there were added 20.43 g of tetramisole. The whole was stirred and heated to reflux and additionally stirred at reflux for 10 minutes. The mixture was further stirred for 4 hours while the temperature was allowed to reach room temperature. The precipitate was filtered off, washed with 100 ml of 2-propanone and 5 ml of water and dried under vacuo at 50° C., yielding 25.55 g of levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) (yield 98%) αD20 =-62.4° (c5. 1N HCl); mp. 127.3°-129° C.
Identifiers
|
REACTION_CXSMILES
|
COC1C=CC(S(N[C@H](C(O)=O)CCC(O)=O)(=O)=O)=CC=1.[CH:22]1[CH:23]=[CH:24][C:25]([CH:28]2[N:35]=[C:34]3[N:30]([CH2:31][CH2:32][S:33]3)[CH2:29]2)=[CH:26][CH:27]=1>CC(=O)C.O>[CH:22]1[CH:27]=[CH:26][C:25]([C@@H:28]2[N:35]=[C:34]3[N:30]([CH2:31][CH2:32][S:33]3)[CH2:29]2)=[CH:24][CH:23]=1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0.1 mol
|
|
Type
|
reactant
|
|
Smiles
|
COC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CCC(=O)O)C(=O)O
|
|
Name
|
|
|
Quantity
|
400 mL
|
|
Type
|
solvent
|
|
Smiles
|
CC(C)=O
|
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Two
|
Name
|
|
|
Quantity
|
20.43 g
|
|
Type
|
reactant
|
|
Smiles
|
C=1C=CC(=CC1)C2CN3CCSC3=N2
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
was stirred
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
heated till all solid
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
The whole was stirred
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
heated
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to reflux
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
additionally stirred
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
at reflux for 10 minutes
|
|
Duration
|
10 min
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
The mixture was further stirred for 4 hours while the temperature
|
|
Duration
|
4 h
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to reach room temperature
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The precipitate was filtered off
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with 100 ml of 2-propanone and 5 ml of water
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried under vacuo at 50° C.
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C=1C=CC(=CC1)[C@H]2CN3CCSC3=N2
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 25.55 g | |
| YIELD: CALCULATEDPERCENTYIELD | 125.1% |
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. |
