Tetramisole
货号 B1196661
分子量: 204.29 g/mol
InChI 键: HLFSDGLLUJUHTE-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
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.
[Compound]
Name
L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid
Quantity
15.9 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.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
|
[Compound]
|
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.
[Compound]
Name
L-N-[(4-methoxyphenyl)sulfonyl]glutamic acid
Quantity
15.9 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.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
|
[Compound]
|
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. |
