Dapsone-D8 (Major)
カタログ番号 B015186
分子量: 256.35 g/mol
InChIキー: MQJKPEGWNLWLTK-PGRXLJNUSA-N
注意: 研究専用です。人間または獣医用ではありません。
Patent
US07531694B2
Procedure details
In a hydrogenation vessel 4-(4′-Nitro-benzenesulfonyl)-phenylamine (100 g), p-toluensulfonic acid (68.4 g), methanol (350 ml), water (150 ml) and 10% palladium on charcoal (7.6 g) are charge. The mixture is allowed to react with hydrogen at approximately 50° C. and 5 bar pressure. At reaction completion, hydrochloric acid is added, the catalyst is filtered and dried. 82 g of crude Dapsone are obtained (82% yield; >99.5% purity).
Name
Yield
82%
Identifiers
|
REACTION_CXSMILES
|
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H].Cl>[Pd].O.CO>[CH:17]1[C:16]([NH2:19])=[CH:15][CH:14]=[C:13]([S:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH:18]=1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
100 g
|
|
Type
|
reactant
|
|
Smiles
|
[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)N
|
|
Name
|
|
|
Quantity
|
68.4 g
|
|
Type
|
reactant
|
|
Smiles
|
C1(=CC=C(C=C1)S(=O)(=O)O)C
|
|
Name
|
|
|
Quantity
|
7.6 g
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
|
Name
|
|
|
Quantity
|
150 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
|
Name
|
|
|
Quantity
|
350 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Step Three
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
Cl
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
is added
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the catalyst is filtered
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C1=CC(=CC=C1N)S(=O)(=O)C=2C=CC(=CC2)N
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 82 g | |
| YIELD: PERCENTYIELD | 82% | |
| YIELD: CALCULATEDPERCENTYIELD | 91.9% |
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
US07531694B2
Procedure details
In a hydrogenation vessel 4-(4′-Nitro-benzenesulfonyl)-phenylamine (100 g), p-toluensulfonic acid (68.4 g), methanol (350 ml), water (150 ml) and 10% palladium on charcoal (7.6 g) are charge. The mixture is allowed to react with hydrogen at approximately 50° C. and 5 bar pressure. At reaction completion, hydrochloric acid is added, the catalyst is filtered and dried. 82 g of crude Dapsone are obtained (82% yield; >99.5% purity).
Name
Yield
82%
Identifiers
|
REACTION_CXSMILES
|
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H].Cl>[Pd].O.CO>[CH:17]1[C:16]([NH2:19])=[CH:15][CH:14]=[C:13]([S:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH:18]=1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
100 g
|
|
Type
|
reactant
|
|
Smiles
|
[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)N
|
|
Name
|
|
|
Quantity
|
68.4 g
|
|
Type
|
reactant
|
|
Smiles
|
C1(=CC=C(C=C1)S(=O)(=O)O)C
|
|
Name
|
|
|
Quantity
|
7.6 g
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
|
Name
|
|
|
Quantity
|
150 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
|
Name
|
|
|
Quantity
|
350 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Step Three
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
Cl
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
is added
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the catalyst is filtered
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C1=CC(=CC=C1N)S(=O)(=O)C=2C=CC(=CC2)N
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 82 g | |
| YIELD: PERCENTYIELD | 82% | |
| YIELD: CALCULATEDPERCENTYIELD | 91.9% |
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
US07531694B2
Procedure details
In a hydrogenation vessel 4-(4′-Nitro-benzenesulfonyl)-phenylamine (100 g), p-toluensulfonic acid (68.4 g), methanol (350 ml), water (150 ml) and 10% palladium on charcoal (7.6 g) are charge. The mixture is allowed to react with hydrogen at approximately 50° C. and 5 bar pressure. At reaction completion, hydrochloric acid is added, the catalyst is filtered and dried. 82 g of crude Dapsone are obtained (82% yield; >99.5% purity).
Name
Yield
82%
Identifiers
|
REACTION_CXSMILES
|
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H].Cl>[Pd].O.CO>[CH:17]1[C:16]([NH2:19])=[CH:15][CH:14]=[C:13]([S:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH:18]=1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
100 g
|
|
Type
|
reactant
|
|
Smiles
|
[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)N
|
|
Name
|
|
|
Quantity
|
68.4 g
|
|
Type
|
reactant
|
|
Smiles
|
C1(=CC=C(C=C1)S(=O)(=O)O)C
|
|
Name
|
|
|
Quantity
|
7.6 g
|
|
Type
|
catalyst
|
|
Smiles
|
[Pd]
|
|
Name
|
|
|
Quantity
|
150 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
|
Name
|
|
|
Quantity
|
350 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Step Three
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
Cl
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
is added
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the catalyst is filtered
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C1=CC(=CC=C1N)S(=O)(=O)C=2C=CC(=CC2)N
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 82 g | |
| YIELD: PERCENTYIELD | 82% | |
| YIELD: CALCULATEDPERCENTYIELD | 91.9% |
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. |
