Fexinidazole
货号 B1672616
分子量: 279.32 g/mol
InChI 键: MIWWSGDADVMLTG-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US04042705
Procedure details
5.8 g (0.02 mols) of 1-methyl-2-(4-thiocyanatophenyloxymethyl)-5-nitro-imidazole are introduced portionwise while stirring, under a nitrogen atmosphere, at room temperature, into a mixture of 26.5 ml of concentrated sulfuric acid and 5.0 g (0.04 mol) of dimethylsulfate and allowed to stand overnight at room temperature. The solution is then heated to 60° C. for 30 minutes, cooled and poured onto ice/water. The precipiate is suction-filtered and washed with water. In addition to bis-4,4'-(1-methyl-5-nitro-imidazolyl-2-methoxy)-diphenyl disulfide (m.p. 160° C.), column chromatographical purification on silica gel yields the 1-methyl-2-(4-methylthiophenyl-oxymethyl)-5-nitro-imidazole, m.p. 116° C.
Name
1-methyl-2-(4-thiocyanatophenyloxymethyl)-5-nitro-imidazole
Quantity
5.8 g
Type
reactant
Reaction Step One
Identifiers
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REACTION_CXSMILES
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[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:19]#N)=[CH:14][CH:13]=1.S(=O)(=O)(O)O.COS(OC)(=O)=O>>[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1
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Inputs
Step One
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Name
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1-methyl-2-(4-thiocyanatophenyloxymethyl)-5-nitro-imidazole
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Quantity
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5.8 g
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|
Type
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reactant
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|
Smiles
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CN1C(=NC=C1[N+](=O)[O-])COC1=CC=C(C=C1)SC#N
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Step Two
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Name
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|
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Quantity
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26.5 mL
|
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Type
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reactant
|
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Smiles
|
S(O)(O)(=O)=O
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|
Name
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|
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Quantity
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5 g
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|
Type
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reactant
|
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Smiles
|
COS(=O)(=O)OC
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Conditions
Temperature
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Control Type
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UNSPECIFIED
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Setpoint
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60 °C
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Other
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Conditions are dynamic
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1
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Details
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See reaction.notes.procedure_details.
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Workups
TEMPERATURE
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Type
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TEMPERATURE
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|
Details
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cooled
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ADDITION
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Type
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ADDITION
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Details
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poured onto ice/water
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FILTRATION
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Type
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FILTRATION
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Details
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The precipiate is suction-filtered
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WASH
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Type
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WASH
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|
Details
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washed with water
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ADDITION
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Type
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ADDITION
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|
Details
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In addition
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CUSTOM
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Type
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CUSTOM
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|
Details
|
to bis-4,4'-(1-methyl-5-nitro-imidazolyl-2-methoxy)-diphenyl disulfide (m.p. 160° C.), column chromatographical purification on silica gel
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Outcomes
Product
Details
Reaction Time |
8 (± 8) h |
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Name
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|
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Type
|
product
|
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Smiles
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CN1C(=NC=C1[N+](=O)[O-])COC1=CC=C(C=C1)SC
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Source
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Source
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Open Reaction Database (ORD) |
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Description
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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. |
