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molecular formula C12H12N2O2S B015186 Dapsone-D8 (Major) CAS No. 557794-38-4

Dapsone-D8 (Major)

Cat. No. B015186
M. Wt: 256.35 g/mol
InChI Key: MQJKPEGWNLWLTK-PGRXLJNUSA-N
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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%.
Quantity
20 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
10 mL
Type
solvent
Reaction Step Three
Quantity
70 mL
Type
solvent
Reaction Step Four
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Five
Name
Quantity
17.8 g
Type
solvent
Reaction Step Six

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%.
Quantity
20 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
10 mL
Type
solvent
Reaction Step Three
Quantity
70 mL
Type
solvent
Reaction Step Four
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Five
Name
Quantity
17.8 g
Type
solvent
Reaction Step Six

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%.
Quantity
20 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
10 mL
Type
solvent
Reaction Step Three
Quantity
70 mL
Type
solvent
Reaction Step Four
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Five
Name
Quantity
17.8 g
Type
solvent
Reaction Step Six

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.
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