Sodium hydride → HCID 23660685, compound

HRID 1670867Notes

Reaction equation

HRID 1670867 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH:12]=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.Cl.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:33]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]1([C:7]2[N:8]([S:38]([C:34]3[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=3)(=[O:40])=[O:39])[CH:9]=[C:10]([CH:12]=[O:13])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 516892Sodium BicarbonateHCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 178519858HCID 178519858, compound

Product 1

HCID 23660685HCID 23660685, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (1.00 g) in tetrahydrofuran (50 mL) was added sodium hydride (60% in oil, 697 mg) at room temperature, and the mixture was stirred for 30 min. 15-Crown-5 (3.84 g) was added dropwise, and the mixture was further stirred for 10 min. 3-Pyridylsulfonyl chloride hydrochloride (1.62 g) was added to the reaction mixture, and the mixture was stirred for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:2→42:3), and the obtained oil was crystallized from diisopropyl ether to give the title compound as colorless crystals (yield 754 mg, 41%).

Workup

  1. stirringthe mixture was further stirred for 10 min
  2. stirringthe mixture was stirred for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:2→42:3)
  8. customthe obtained oil was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-0b26cb1587824d17ab4392e35d35b003
Source dataset
uspto-grants-2011_08
Patent number
US07994205B2

Reaction notes

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