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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

To a refluxing solution of 20.43 g of tetramisole (0.1 mol) in 190 ml of 2-propanone and 10 ml. of water was added 15.9 g of L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (0.05 mol). The mixture was refluxed for another 5 minutes and cooled to 15° C. After 12 hours the precipitate was filtered off, washed with 2-propanone and dried under vacuo at 70° C., yielding 23.88 g of levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) (yield=91.6%) αD20 =-63.5° (c5, 1N HCl); mp. 127.6°-129.3° C.
Quantity
20.43 g
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid
Quantity
15.9 g
Type
reactant
Reaction Step Two
Quantity
190 mL
Type
solvent
Reaction Step Three

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.O>CC(=O)C>[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
Quantity
20.43 g
Type
reactant
Smiles
C=1C=CC(=CC1)C2CN3CCSC3=N2
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O
Name
L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid
Quantity
15.9 g
Type
reactant
Smiles
Step Three
Name
Quantity
190 mL
Type
solvent
Smiles
CC(C)=O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
15 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The mixture was refluxed for another 5 minutes
Duration
5 min
FILTRATION
Type
FILTRATION
Details
After 12 hours the precipitate was filtered off
Duration
12 h
WASH
Type
WASH
Details
washed with 2-propanone
CUSTOM
Type
CUSTOM
Details
dried under vacuo at 70° C.

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC(=CC1)[C@H]2CN3CCSC3=N2
Measurements
Type Value Analysis
AMOUNT: MASS 23.88 g
YIELD: CALCULATEDPERCENTYIELD 116.9%

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

To a refluxing solution of 20.43 g of tetramisole (0.1 mol) in 190 ml of 2-propanone and 10 ml. of water was added 15.9 g of L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (0.05 mol). The mixture was refluxed for another 5 minutes and cooled to 15° C. After 12 hours the precipitate was filtered off, washed with 2-propanone and dried under vacuo at 70° C., yielding 23.88 g of levamisole.L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid (salt) (yield=91.6%) αD20 =-63.5° (c5, 1N HCl); mp. 127.6°-129.3° C.
Quantity
20.43 g
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid
Quantity
15.9 g
Type
reactant
Reaction Step Two
Quantity
190 mL
Type
solvent
Reaction Step Three

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.O>CC(=O)C>[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
Quantity
20.43 g
Type
reactant
Smiles
C=1C=CC(=CC1)C2CN3CCSC3=N2
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O
Name
L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid
Quantity
15.9 g
Type
reactant
Smiles
Step Three
Name
Quantity
190 mL
Type
solvent
Smiles
CC(C)=O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
15 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The mixture was refluxed for another 5 minutes
Duration
5 min
FILTRATION
Type
FILTRATION
Details
After 12 hours the precipitate was filtered off
Duration
12 h
WASH
Type
WASH
Details
washed with 2-propanone
CUSTOM
Type
CUSTOM
Details
dried under vacuo at 70° C.

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC(=CC1)[C@H]2CN3CCSC3=N2
Measurements
Type Value Analysis
AMOUNT: MASS 23.88 g
YIELD: CALCULATEDPERCENTYIELD 116.9%

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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