Tetramisole
Cat. No. B1196661
M. Wt: 204.29 g/mol
InChI Key: HLFSDGLLUJUHTE-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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-propanol 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 till an homogeneous solution was obtained. The solution 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-propanol and 5 ml of water and dried under vacuo at 50° C., yielding 26.17 g levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) (yield 100.3%) αD20 =-62.8° (c5. 1N HCl); mp. 127.4°-129.1° C.
[Compound]
Name
L-N-[(4-methoxyphenyl)sulfonyl]-glutamic acid
Quantity
31.73 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[CH:1]1[CH:2]=[CH:3][C:4]([CH:7]2[N:14]=[C:13]3[N:9]([CH2:10][CH2:11][S:12]3)[CH2:8]2)=[CH:5][CH:6]=1>CC(O)C.O>[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[N:14]=[C:13]3[N:9]([CH2:10][CH2:11][S:12]3)[CH2:8]2)=[CH:3][CH:2]=1
|
Inputs
Step One
[Compound]
|
Name
|
L-N-[(4-methoxyphenyl)sulfonyl]-glutamic acid
|
|
Quantity
|
31.73 g
|
|
Type
|
reactant
|
|
Smiles
|
|
|
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 till an homogeneous solution
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
was obtained
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
The solution 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-propanol 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 | 26.17 g | |
| YIELD: CALCULATEDPERCENTYIELD | 128.1% |
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-propanol 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 till an homogeneous solution was obtained. The solution 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-propanol and 5 ml of water and dried under vacuo at 50° C., yielding 26.17 g levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) (yield 100.3%) αD20 =-62.8° (c5. 1N HCl); mp. 127.4°-129.1° C.
[Compound]
Name
L-N-[(4-methoxyphenyl)sulfonyl]-glutamic acid
Quantity
31.73 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[CH:1]1[CH:2]=[CH:3][C:4]([CH:7]2[N:14]=[C:13]3[N:9]([CH2:10][CH2:11][S:12]3)[CH2:8]2)=[CH:5][CH:6]=1>CC(O)C.O>[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[N:14]=[C:13]3[N:9]([CH2:10][CH2:11][S:12]3)[CH2:8]2)=[CH:3][CH:2]=1
|
Inputs
Step One
[Compound]
|
Name
|
L-N-[(4-methoxyphenyl)sulfonyl]-glutamic acid
|
|
Quantity
|
31.73 g
|
|
Type
|
reactant
|
|
Smiles
|
|
|
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 till an homogeneous solution
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
was obtained
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
The solution 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-propanol 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 | 26.17 g | |
| YIELD: CALCULATEDPERCENTYIELD | 128.1% |
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. |
