Sodium Iodide → HCID 22911266, compound

HRID 1378384Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:9][C:10]1[C:11]([N+:17]([O-:19])=[O:18])=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1.[C:20]1([C:26]2[N:27]=[CH:28][N:29]([CH2:31][CH2:32][CH2:33]Cl)[CH:30]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[N+:17]([C:11]1[C:12]([O:16][CH2:33][CH2:32][CH2:31][N:29]2[CH:30]=[C:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:27]=[CH:28]2)=[CH:13][CH:14]=[CH:15][C:10]=1[CH3:9])([O-:19])=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

9.02 g of potassium carbonate and a catalytic amount of sodium iodide were added to a dimethylformamide solution of 5 g of 3-methyl-2-nitrophenol and 7.2 g of 4-phenyl-1-(3-chloropropyl)-1H-imidazole. The obtained mixture was heated at 100° C. for 2 hours to conduct a reaction. After the completion of the reaction, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and distilled to remove the solvent. The obtained oily substance .was purified by silica gel chromatography to give 9.91 g of 2-nitro-3-[3-(4-phenyl-1H-imidazol-1-yl)propoxy]toluene. This product was catalytically reduced and condensed with butyl isocyanate according to a conventional process to give 11.2 g of the title compound having a melting point of 102° to 110° C.

Workup

customa reaction
customAfter the completion of the reaction
extractionthe reaction mixture was extracted with ethyl acetate
dry with materialThe ethyl acetate layer was dried over magnesium sulfate
distillationdistilled
customto remove the solvent
customThe obtained oily substance .was purified by silica gel chromatography

Sources & evidence

ORD record: ord-2e226892d1774d61b2cf6bc863d28c26
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668136

Reaction notes

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