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molecular formula C12H13N3O3S B1672616 Fexinidazole CAS No. 59729-37-2

Fexinidazole

Cat. No. B1672616
M. Wt: 279.32 g/mol
InChI Key: MIWWSGDADVMLTG-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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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
Quantity
26.5 mL
Type
reactant
Reaction Step Two
Quantity
5 g
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[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

Inputs

Step One
Name
1-methyl-2-(4-thiocyanatophenyloxymethyl)-5-nitro-imidazole
Quantity
5.8 g
Type
reactant
Smiles
CN1C(=NC=C1[N+](=O)[O-])COC1=CC=C(C=C1)SC#N
Step Two
Name
Quantity
26.5 mL
Type
reactant
Smiles
S(O)(O)(=O)=O
Name
Quantity
5 g
Type
reactant
Smiles
COS(=O)(=O)OC

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
60 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
cooled
ADDITION
Type
ADDITION
Details
poured onto ice/water
FILTRATION
Type
FILTRATION
Details
The precipiate is suction-filtered
WASH
Type
WASH
Details
washed with water
ADDITION
Type
ADDITION
Details
In addition
CUSTOM
Type
CUSTOM
Details
to bis-4,4'-(1-methyl-5-nitro-imidazolyl-2-methoxy)-diphenyl disulfide (m.p. 160° C.), column chromatographical purification on silica gel

Outcomes

Product
Details
Reaction Time
8 (± 8) h
Name
Type
product
Smiles
CN1C(=NC=C1[N+](=O)[O-])COC1=CC=C(C=C1)SC

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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