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molecular formula C12H15N3O2S B1528130 Albendazole-D3 CAS No. 1353867-92-1

Albendazole-D3

Cat. No. B1528130
M. Wt: 268.35 g/mol
InChI Key: HXHWSAZORRCQMX-BMSJAHLVSA-N
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Patent
US04152522

Procedure details

Preparation of methyl 5-propylthio-2-benzimidazole carbamate--A 1.82 g portion of cyanamide was dissolved in 10 ml of water. Methyl chloroformate, 4.64 g, and 6.34 g of 50% aqueous sodium hydroxide in 6 ml of water were added simultaneously so as to maintain the pH at approximately 7 as determined by a pH meter. The reaction mixture was stirred at 50° C. for one hour. A portion of 7.4 g of concentrated hydrochloric acid in 7 ml of water was added until the pH was 4. The methanol solution of 4-propylthio-o-phenylenediamine from Example IV was added at once. More of the hydrochloric acid solution was added to adjust the pH to 4. The reaction mixture was heated to distill the methanol. As methanol was nearly removed more hydrochloric acid solution was added to keep the pH at 4. Water was added from time to time to keep the slurry from becoming too thick. The reaction slurry was heated at 100° C. for one hour after the methanol had been removed. The reaction slurry was cooled, filtered and washed liberally with water. The solids were air dried to produce 8.77 g of crude methyl 5-propylthio-2-benzimidazole carbamate. The crude solids were washed 3 times with cold acetone and dried to produce 7.52 g of product assaying 97% methyl-5-propylthio-2-benzimidazole carbamate by HPLC, 73% yield from the 4-propylthio-2-nitroaniline employed in Example IV.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
[Compound]
Name
methyl 5-propylthio-2-benzimidazole carbamate--A
Quantity
1.82 g
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
6.34 g
Type
reactant
Reaction Step Three
Name
Quantity
6 mL
Type
solvent
Reaction Step Three
Quantity
7.4 g
Type
reactant
Reaction Step Four
Name
Quantity
7 mL
Type
solvent
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Name
Quantity
10 mL
Type
solvent
Reaction Step Six

Identifiers

REACTION_CXSMILES
[N:1]#[C:2]N.Cl[C:5]([O:7][CH3:8])=[O:6].[OH-].[Na+].Cl.[CH2:12]([S:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([NH2:23])[CH:17]=1)[CH2:13][CH3:14]>O.CO>[CH2:12]([S:15][C:16]1[CH:21]=[CH:20][C:19]2[N:22]=[C:2]([NH:1][C:5]([O:7][CH3:8])=[O:6])[NH:23][C:18]=2[CH:17]=1)[CH2:13][CH3:14] |f:2.3|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(CC)SC1=CC(=C(C=C1)N)N
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Two
Name
methyl 5-propylthio-2-benzimidazole carbamate--A
Quantity
1.82 g
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
N#CN
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC(=O)OC
Name
Quantity
6.34 g
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
6 mL
Type
solvent
Smiles
O
Step Four
Name
Quantity
7.4 g
Type
reactant
Smiles
Cl
Name
Quantity
7 mL
Type
solvent
Smiles
O
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl
Step Six
Name
Quantity
10 mL
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
50 °C
Stirring
Type
CUSTOM
Details
The reaction mixture was stirred at 50° C. for one hour
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
to maintain the pH at approximately 7
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was heated
DISTILLATION
Type
DISTILLATION
Details
to distill the methanol
CUSTOM
Type
CUSTOM
Details
As methanol was nearly removed more hydrochloric acid solution
ADDITION
Type
ADDITION
Details
was added
ADDITION
Type
ADDITION
Details
Water was added from time to time
TEMPERATURE
Type
TEMPERATURE
Details
The reaction slurry was heated at 100° C. for one hour after the methanol
Duration
1 h
CUSTOM
Type
CUSTOM
Details
had been removed
TEMPERATURE
Type
TEMPERATURE
Details
The reaction slurry was cooled
FILTRATION
Type
FILTRATION
Details
filtered
WASH
Type
WASH
Details
washed liberally with water
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
1 h
Name
Type
product
Smiles
C(CC)SC1=CC2=C(N=C(N2)NC(=O)OC)C=C1
Measurements
Type Value Analysis
AMOUNT: MASS 8.77 g

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
US04152522

Procedure details

Preparation of methyl 5-propylthio-2-benzimidazole carbamate--A 1.82 g portion of cyanamide was dissolved in 10 ml of water. Methyl chloroformate, 4.64 g, and 6.34 g of 50% aqueous sodium hydroxide in 6 ml of water were added simultaneously so as to maintain the pH at approximately 7 as determined by a pH meter. The reaction mixture was stirred at 50° C. for one hour. A portion of 7.4 g of concentrated hydrochloric acid in 7 ml of water was added until the pH was 4. The methanol solution of 4-propylthio-o-phenylenediamine from Example IV was added at once. More of the hydrochloric acid solution was added to adjust the pH to 4. The reaction mixture was heated to distill the methanol. As methanol was nearly removed more hydrochloric acid solution was added to keep the pH at 4. Water was added from time to time to keep the slurry from becoming too thick. The reaction slurry was heated at 100° C. for one hour after the methanol had been removed. The reaction slurry was cooled, filtered and washed liberally with water. The solids were air dried to produce 8.77 g of crude methyl 5-propylthio-2-benzimidazole carbamate. The crude solids were washed 3 times with cold acetone and dried to produce 7.52 g of product assaying 97% methyl-5-propylthio-2-benzimidazole carbamate by HPLC, 73% yield from the 4-propylthio-2-nitroaniline employed in Example IV.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
[Compound]
Name
methyl 5-propylthio-2-benzimidazole carbamate--A
Quantity
1.82 g
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
6.34 g
Type
reactant
Reaction Step Three
Name
Quantity
6 mL
Type
solvent
Reaction Step Three
Quantity
7.4 g
Type
reactant
Reaction Step Four
Name
Quantity
7 mL
Type
solvent
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Name
Quantity
10 mL
Type
solvent
Reaction Step Six

Identifiers

REACTION_CXSMILES
[N:1]#[C:2]N.Cl[C:5]([O:7][CH3:8])=[O:6].[OH-].[Na+].Cl.[CH2:12]([S:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([NH2:23])[CH:17]=1)[CH2:13][CH3:14]>O.CO>[CH2:12]([S:15][C:16]1[CH:21]=[CH:20][C:19]2[N:22]=[C:2]([NH:1][C:5]([O:7][CH3:8])=[O:6])[NH:23][C:18]=2[CH:17]=1)[CH2:13][CH3:14] |f:2.3|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(CC)SC1=CC(=C(C=C1)N)N
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Two
Name
methyl 5-propylthio-2-benzimidazole carbamate--A
Quantity
1.82 g
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
N#CN
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC(=O)OC
Name
Quantity
6.34 g
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
6 mL
Type
solvent
Smiles
O
Step Four
Name
Quantity
7.4 g
Type
reactant
Smiles
Cl
Name
Quantity
7 mL
Type
solvent
Smiles
O
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl
Step Six
Name
Quantity
10 mL
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
50 °C
Stirring
Type
CUSTOM
Details
The reaction mixture was stirred at 50° C. for one hour
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
to maintain the pH at approximately 7
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was heated
DISTILLATION
Type
DISTILLATION
Details
to distill the methanol
CUSTOM
Type
CUSTOM
Details
As methanol was nearly removed more hydrochloric acid solution
ADDITION
Type
ADDITION
Details
was added
ADDITION
Type
ADDITION
Details
Water was added from time to time
TEMPERATURE
Type
TEMPERATURE
Details
The reaction slurry was heated at 100° C. for one hour after the methanol
Duration
1 h
CUSTOM
Type
CUSTOM
Details
had been removed
TEMPERATURE
Type
TEMPERATURE
Details
The reaction slurry was cooled
FILTRATION
Type
FILTRATION
Details
filtered
WASH
Type
WASH
Details
washed liberally with water
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
1 h
Name
Type
product
Smiles
C(CC)SC1=CC2=C(N=C(N2)NC(=O)OC)C=C1
Measurements
Type Value Analysis
AMOUNT: MASS 8.77 g

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
US04152522

Procedure details

Preparation of methyl 5-propylthio-2-benzimidazole carbamate--A 1.82 g portion of cyanamide was dissolved in 10 ml of water. Methyl chloroformate, 4.64 g, and 6.34 g of 50% aqueous sodium hydroxide in 6 ml of water were added simultaneously so as to maintain the pH at approximately 7 as determined by a pH meter. The reaction mixture was stirred at 50° C. for one hour. A portion of 7.4 g of concentrated hydrochloric acid in 7 ml of water was added until the pH was 4. The methanol solution of 4-propylthio-o-phenylenediamine from Example IV was added at once. More of the hydrochloric acid solution was added to adjust the pH to 4. The reaction mixture was heated to distill the methanol. As methanol was nearly removed more hydrochloric acid solution was added to keep the pH at 4. Water was added from time to time to keep the slurry from becoming too thick. The reaction slurry was heated at 100° C. for one hour after the methanol had been removed. The reaction slurry was cooled, filtered and washed liberally with water. The solids were air dried to produce 8.77 g of crude methyl 5-propylthio-2-benzimidazole carbamate. The crude solids were washed 3 times with cold acetone and dried to produce 7.52 g of product assaying 97% methyl-5-propylthio-2-benzimidazole carbamate by HPLC, 73% yield from the 4-propylthio-2-nitroaniline employed in Example IV.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
[Compound]
Name
methyl 5-propylthio-2-benzimidazole carbamate--A
Quantity
1.82 g
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
6.34 g
Type
reactant
Reaction Step Three
Name
Quantity
6 mL
Type
solvent
Reaction Step Three
Quantity
7.4 g
Type
reactant
Reaction Step Four
Name
Quantity
7 mL
Type
solvent
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Name
Quantity
10 mL
Type
solvent
Reaction Step Six

Identifiers

REACTION_CXSMILES
[N:1]#[C:2]N.Cl[C:5]([O:7][CH3:8])=[O:6].[OH-].[Na+].Cl.[CH2:12]([S:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([NH2:23])[CH:17]=1)[CH2:13][CH3:14]>O.CO>[CH2:12]([S:15][C:16]1[CH:21]=[CH:20][C:19]2[N:22]=[C:2]([NH:1][C:5]([O:7][CH3:8])=[O:6])[NH:23][C:18]=2[CH:17]=1)[CH2:13][CH3:14] |f:2.3|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(CC)SC1=CC(=C(C=C1)N)N
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Two
Name
methyl 5-propylthio-2-benzimidazole carbamate--A
Quantity
1.82 g
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
N#CN
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC(=O)OC
Name
Quantity
6.34 g
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
6 mL
Type
solvent
Smiles
O
Step Four
Name
Quantity
7.4 g
Type
reactant
Smiles
Cl
Name
Quantity
7 mL
Type
solvent
Smiles
O
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl
Step Six
Name
Quantity
10 mL
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
50 °C
Stirring
Type
CUSTOM
Details
The reaction mixture was stirred at 50° C. for one hour
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
to maintain the pH at approximately 7
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was heated
DISTILLATION
Type
DISTILLATION
Details
to distill the methanol
CUSTOM
Type
CUSTOM
Details
As methanol was nearly removed more hydrochloric acid solution
ADDITION
Type
ADDITION
Details
was added
ADDITION
Type
ADDITION
Details
Water was added from time to time
TEMPERATURE
Type
TEMPERATURE
Details
The reaction slurry was heated at 100° C. for one hour after the methanol
Duration
1 h
CUSTOM
Type
CUSTOM
Details
had been removed
TEMPERATURE
Type
TEMPERATURE
Details
The reaction slurry was cooled
FILTRATION
Type
FILTRATION
Details
filtered
WASH
Type
WASH
Details
washed liberally with water
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
1 h
Name
Type
product
Smiles
C(CC)SC1=CC2=C(N=C(N2)NC(=O)OC)C=C1
Measurements
Type Value Analysis
AMOUNT: MASS 8.77 g

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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