Sodium hydride → HCID 23660681, compound

HRID 2359958Notes

Reaction equation

HRID 2359958 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+].[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[S:21](Cl)(=[O:23])=[O:22].C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]1([C:7]2[N:8]([S:21]([C:17]3[S:16][CH:20]=[CH:19][CH:18]=3)(=[O:23])=[O:22])[CH:9]=[C:10]([CH:12]=[O:13])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 855182-Thiophenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 178519858HCID 178519858, compound

Product 1

HCID 23660681HCID 23660681, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (1.73 g) in tetrahydrofuran (100 mL) was added sodium hydride (60% in oil, 603 mg) at room temperature, and the mixture was stirred for 15 min. Thiophene-2-sulfonyl chloride (2.39 g) was added to the reaction mixture, and the mixture was stirred for 1 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→2:3) to give the title compound as a colorless oil (yield 750 mg, 23%).

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:2→2:3)

Sources & evidence

ORD record
ord-a67569844a4243f79723a6b9d09ba14f
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

Loading…