Water → HCID 178504866, compound

HRID 1595414Notes

Reaction equation

[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:23]([NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)=[O:24])=[CH:5][CH:4]=1.[CH3:31][S:32]([O-:34])=[O:33].[Na+].O>CN(C)C=O>[ClH:1].[CH3:31][S:32]([O:34][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:23]([NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)=[O:24])=[CH:5][CH:4]=1)=[O:33]

Participants

Conditions

Temperature: 80 °C

Procedure

5-(4-Chloromethylphenyl)-2-(4-nitrophenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (700 mg) obtained in Example 94 and sodium methanesulfinate (325 mg) were dissolved in dimethylformamide (30 ml) and the mixture was stirred at 80° C. for 1 hr. The mixture was poured into water (100 ml) and extracted with ethyl acetate. The ethyl acetate layer was washed with water and, after drying, the solvent was evaporated. The obtained residue was suspended in acetone (30 ml) and 1 M hydrochloric acid—ether solution (3 ml) was added. The solvent was evaporated and the obtained residue was recrystallized from acetone to give 5-(4-methanesulfinyloxymethylphenyl)-2-(4-nitrophenyl)-N-(2-thiazolyl) imidazole-4-carboxamide hydrochloride (736 mg), melting point 278-282° C. (decomposition).

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with water
customafter drying
customthe solvent was evaporated
addition1 M hydrochloric acid—ether solution (3 ml) was added
customThe solvent was evaporated
customthe obtained residue was recrystallized from acetone

Sources & evidence

ORD record: ord-70b295444da6434cb33cf4e3e833f0e8
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

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