Dapsone-D8 (Major)
Numéro de catalogue B015186
Poids moléculaire: 256.35 g/mol
Clé InChI: MQJKPEGWNLWLTK-PGRXLJNUSA-N
Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.
Patent
US09079831B2
Procedure details
In autoclave at room temperature 4,4′-dinitrodiphenylsulfone (0.0649 mol, 20.0 g), 5% palladium on 50% wet carbon (1.4 g), 70% methanesulfonic acid in water (0.130 mol, 17.8 g), water (10 ml) and methanol (70 ml) are loaded. The mixture is left to react under hydrogen pressure (4-5 atm) at a temperature of 55-60° C. for about 8 hours. The mixture is filtered on a Perlite layer washing with methanol (10 ml for 2 times), subsequently with water (80 ml). The solution is concentrated under reduced volume to remove the organic phase. The aqueous phase is extracted with ethyl acetate (50 ml for 3 times) and the organic washings are discarded. Discolouring carbon (1.0 g) is added under vigorous stirring and after 15-20 minutes the mixture is filtered on a Perlite layer. To the aqueous solution heated at about 50° C. a aqueous solution of 30% sodium hydroxide is slowly added to reach a pH higher than 10. After about 30 minutes the mixture is cooled to 0-5° C. and then filtered, washing the solid with water cooled at 0-5° C. (20 ml for three times). After oven-drying at 50° C., 11.2 g of crude Dapsone are obtained that are then crystallized from a mixture of isopropanol (35 ml) and water (25 ml) to obtain 10.2 g of dry Dapsone, having a chemical purity evaluated by HPLC equal to about 98.5%.
Name
Identifiers
|
REACTION_CXSMILES
|
[CH:1]1[C:6]([N+:7]([O-])=O)=[CH:5][CH:4]=[C:3]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:2]=1.CS(O)(=O)=O>O.CO.[Pd]>[CH:17]1[C:16]([NH2:19])=[CH:15][CH:14]=[C:13]([S:10]([C:3]2[CH:2]=[CH:1][C:6]([NH2:7])=[CH:5][CH:4]=2)(=[O:12])=[O:11])[CH:18]=1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
20 g
|
|
Type
|
reactant
|
|
Smiles
|
C1=CC(=CC=C1[N+](=O)[O-])S(=O)(=O)C2=CC=C(C=C2)[N+](=O)[O-]
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CS(=O)(=O)O
|
Step Three
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Four
|
Name
|
|
|
Quantity
|
70 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Step Five
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
Step Six
|
Name
|
|
|
Quantity
|
17.8 g
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
50 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
under vigorous stirring and after 15-20 minutes the mixture
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
at room temperature
|
WAIT
|
Type
|
WAIT
|
|
Details
|
The mixture is left
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to react under hydrogen pressure (4-5 atm) at a temperature of 55-60° C. for about 8 hours
|
|
Duration
|
8 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The mixture is filtered on a Perlite layer
|
WASH
|
Type
|
WASH
|
|
Details
|
washing with methanol (10 ml for 2 times), subsequently with water (80 ml)
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The solution is concentrated under reduced volume
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to remove the organic phase
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
The aqueous phase is extracted with ethyl acetate (50 ml for 3 times)
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
Discolouring carbon (1.0 g) is added
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
is filtered on a Perlite layer
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
is slowly added
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
After about 30 minutes the mixture is cooled to 0-5° C.
|
|
Duration
|
30 min
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
washing the solid with water
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
cooled at 0-5° C. (20 ml for three times)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
After oven-drying at 50° C.
|
Outcomes
Product
Details
Reaction Time |
17.5 (± 2.5) min |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C1=CC(=CC=C1N)S(=O)(=O)C=2C=CC(=CC2)N
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 11.2 g | |
| YIELD: CALCULATEDPERCENTYIELD | 69.5% |
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
US09079831B2
Procedure details
In autoclave at room temperature 4,4′-dinitrodiphenylsulfone (0.0649 mol, 20.0 g), 5% palladium on 50% wet carbon (1.4 g), 70% methanesulfonic acid in water (0.130 mol, 17.8 g), water (10 ml) and methanol (70 ml) are loaded. The mixture is left to react under hydrogen pressure (4-5 atm) at a temperature of 55-60° C. for about 8 hours. The mixture is filtered on a Perlite layer washing with methanol (10 ml for 2 times), subsequently with water (80 ml). The solution is concentrated under reduced volume to remove the organic phase. The aqueous phase is extracted with ethyl acetate (50 ml for 3 times) and the organic washings are discarded. Discolouring carbon (1.0 g) is added under vigorous stirring and after 15-20 minutes the mixture is filtered on a Perlite layer. To the aqueous solution heated at about 50° C. a aqueous solution of 30% sodium hydroxide is slowly added to reach a pH higher than 10. After about 30 minutes the mixture is cooled to 0-5° C. and then filtered, washing the solid with water cooled at 0-5° C. (20 ml for three times). After oven-drying at 50° C., 11.2 g of crude Dapsone are obtained that are then crystallized from a mixture of isopropanol (35 ml) and water (25 ml) to obtain 10.2 g of dry Dapsone, having a chemical purity evaluated by HPLC equal to about 98.5%.
Name
Identifiers
|
REACTION_CXSMILES
|
[CH:1]1[C:6]([N+:7]([O-])=O)=[CH:5][CH:4]=[C:3]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:2]=1.CS(O)(=O)=O>O.CO.[Pd]>[CH:17]1[C:16]([NH2:19])=[CH:15][CH:14]=[C:13]([S:10]([C:3]2[CH:2]=[CH:1][C:6]([NH2:7])=[CH:5][CH:4]=2)(=[O:12])=[O:11])[CH:18]=1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
20 g
|
|
Type
|
reactant
|
|
Smiles
|
C1=CC(=CC=C1[N+](=O)[O-])S(=O)(=O)C2=CC=C(C=C2)[N+](=O)[O-]
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CS(=O)(=O)O
|
Step Three
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Four
|
Name
|
|
|
Quantity
|
70 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Step Five
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
Step Six
|
Name
|
|
|
Quantity
|
17.8 g
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
50 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
under vigorous stirring and after 15-20 minutes the mixture
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
at room temperature
|
WAIT
|
Type
|
WAIT
|
|
Details
|
The mixture is left
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to react under hydrogen pressure (4-5 atm) at a temperature of 55-60° C. for about 8 hours
|
|
Duration
|
8 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The mixture is filtered on a Perlite layer
|
WASH
|
Type
|
WASH
|
|
Details
|
washing with methanol (10 ml for 2 times), subsequently with water (80 ml)
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The solution is concentrated under reduced volume
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to remove the organic phase
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
The aqueous phase is extracted with ethyl acetate (50 ml for 3 times)
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
Discolouring carbon (1.0 g) is added
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
is filtered on a Perlite layer
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
is slowly added
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
After about 30 minutes the mixture is cooled to 0-5° C.
|
|
Duration
|
30 min
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
washing the solid with water
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
cooled at 0-5° C. (20 ml for three times)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
After oven-drying at 50° C.
|
Outcomes
Product
Details
Reaction Time |
17.5 (± 2.5) min |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C1=CC(=CC=C1N)S(=O)(=O)C=2C=CC(=CC2)N
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 11.2 g | |
| YIELD: CALCULATEDPERCENTYIELD | 69.5% |
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
US09079831B2
Procedure details
In autoclave at room temperature 4,4′-dinitrodiphenylsulfone (0.0649 mol, 20.0 g), 5% palladium on 50% wet carbon (1.4 g), 70% methanesulfonic acid in water (0.130 mol, 17.8 g), water (10 ml) and methanol (70 ml) are loaded. The mixture is left to react under hydrogen pressure (4-5 atm) at a temperature of 55-60° C. for about 8 hours. The mixture is filtered on a Perlite layer washing with methanol (10 ml for 2 times), subsequently with water (80 ml). The solution is concentrated under reduced volume to remove the organic phase. The aqueous phase is extracted with ethyl acetate (50 ml for 3 times) and the organic washings are discarded. Discolouring carbon (1.0 g) is added under vigorous stirring and after 15-20 minutes the mixture is filtered on a Perlite layer. To the aqueous solution heated at about 50° C. a aqueous solution of 30% sodium hydroxide is slowly added to reach a pH higher than 10. After about 30 minutes the mixture is cooled to 0-5° C. and then filtered, washing the solid with water cooled at 0-5° C. (20 ml for three times). After oven-drying at 50° C., 11.2 g of crude Dapsone are obtained that are then crystallized from a mixture of isopropanol (35 ml) and water (25 ml) to obtain 10.2 g of dry Dapsone, having a chemical purity evaluated by HPLC equal to about 98.5%.
Name
Identifiers
|
REACTION_CXSMILES
|
[CH:1]1[C:6]([N+:7]([O-])=O)=[CH:5][CH:4]=[C:3]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:2]=1.CS(O)(=O)=O>O.CO.[Pd]>[CH:17]1[C:16]([NH2:19])=[CH:15][CH:14]=[C:13]([S:10]([C:3]2[CH:2]=[CH:1][C:6]([NH2:7])=[CH:5][CH:4]=2)(=[O:12])=[O:11])[CH:18]=1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
20 g
|
|
Type
|
reactant
|
|
Smiles
|
C1=CC(=CC=C1[N+](=O)[O-])S(=O)(=O)C2=CC=C(C=C2)[N+](=O)[O-]
|
Step Two
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CS(=O)(=O)O
|
Step Three
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Four
|
Name
|
|
|
Quantity
|
70 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Step Five
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
Step Six
|
Name
|
|
|
Quantity
|
17.8 g
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
50 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
under vigorous stirring and after 15-20 minutes the mixture
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
at room temperature
|
WAIT
|
Type
|
WAIT
|
|
Details
|
The mixture is left
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to react under hydrogen pressure (4-5 atm) at a temperature of 55-60° C. for about 8 hours
|
|
Duration
|
8 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The mixture is filtered on a Perlite layer
|
WASH
|
Type
|
WASH
|
|
Details
|
washing with methanol (10 ml for 2 times), subsequently with water (80 ml)
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The solution is concentrated under reduced volume
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to remove the organic phase
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
The aqueous phase is extracted with ethyl acetate (50 ml for 3 times)
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
Discolouring carbon (1.0 g) is added
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
is filtered on a Perlite layer
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
is slowly added
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
After about 30 minutes the mixture is cooled to 0-5° C.
|
|
Duration
|
30 min
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
washing the solid with water
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
cooled at 0-5° C. (20 ml for three times)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
After oven-drying at 50° C.
|
Outcomes
Product
Details
Reaction Time |
17.5 (± 2.5) min |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C1=CC(=CC=C1N)S(=O)(=O)C=2C=CC(=CC2)N
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 11.2 g | |
| YIELD: CALCULATEDPERCENTYIELD | 69.5% |
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. |
