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molecular formula C11H12N2S B1196661 Tetramisole CAS No. 5036-02-2

Tetramisole

Cat. No. B1196661
M. Wt: 204.29 g/mol
InChI Key: HLFSDGLLUJUHTE-UHFFFAOYSA-N
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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
Quantity
400 mL
Type
solvent
Reaction Step One
Name
Quantity
20 mL
Type
solvent
Reaction Step One
Quantity
20.43 g
Type
reactant
Reaction Step Two

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
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
Quantity
400 mL
Type
solvent
Reaction Step One
Name
Quantity
20 mL
Type
solvent
Reaction Step One
Quantity
20.43 g
Type
reactant
Reaction Step Two

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
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.
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