Ammonia → HCID 67546981, compound

HRID 2356717Notes

Reaction equation

HRID 2356717 reaction equation
[Cl:1][C:2]1[S:6][CH:5]=[C:4]([C:7]2[NH:8][C:9]([CH2:18][CH3:19])=[C:10]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[N:11]=2)[CH:3]=1.[NH3:20].Cl[S:22]([OH:25])(=[O:24])=[O:23]>>[Cl:1][C:2]1[S:6][C:5]([S:22]([OH:25])(=[O:24])=[O:23])=[C:4]([C:7]2[NH:8][C:9]([CH2:18][CH3:19])=[C:10]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[N:11]=2)[CH:3]=1.[Cl:1][C:2]1[S:6][C:5]([S:22](=[O:25])(=[O:23])[NH2:20])=[C:4]([C:7]2[NH:8][C:9]([CH2:18][CH3:19])=[C:10]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[N:11]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24638Chlorosulfonic acidHCID 59384827HCID 59384827, compound

Product 2

HCID 67546981HCID 67546981, compoundHCID 86593197HCID 86593197, compound

Procedure

A mixture of 2-(5-chlorothiophen-3-yl)-5-ethyl-4-(3-pyridyl)-imidazole (2.00 g) in chlorosulfonic acid (15 ml) was stirred at room temperature for one week. The mixture was slowly added dropwise to 28% aqueous ammonia (500 ml), and the resulting mixture was stirred for 30 minutes and then concentrated under reduced pressure. The resulting residue was dissolved in methanol-tetrahydrofuran (5:1), dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel flush column chromatography (solvent: chloroform:methanol=10:1→2.5:1), and then, by NH silica gel flush column chromatography (solvent: chloroform:methanol=10:1→4:1) to obtain 2-(5-chloro-2-sulfothiophen-3-yl)-5-ethyl-4-(3-pyridyl)imidazole and 2-(5-chloro-2-sulfamoylthiophen-3-yl)-5-ethyl-4-(3-pyridyl)imidazole. Each product was treated with hydrogen chloride-dioxane solution to obtain 2-(5-chloro-2-sulfothiophen-3-yl)-5-ethyl-4-(3-pyridyl)imidazole dihydrochloride (741 mg) and 2-(5-chloro-2-sulfamoylthiophen-3-yl)-5-ethyl-4-(3-pyridyl)imidazole dihydrochloride (105 mg) each as colorless powder.

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in methanol-tetrahydrofuran (5:1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel
  7. customflush column chromatography (solvent: chloroform:methanol=10:1→2.5:1)
  8. customby NH silica gel flush column chromatography (solvent: chloroform:methanol=10:1→4:1)

Sources & evidence

ORD record
ord-0078946607434e9f849df5830f429efa
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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