Water → HCID 18426789, compound

HRID 1281150Notes

Reaction equation

HRID 1281150 reaction equation
[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[N:6]=[C:7]([C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12](Br)=[CH:11][CH:10]=3)[NH:8][C:4]=2[CH:3]=1.C([Li])CCC.CN(C)[CH:30]=[O:31].O>O1CCCC1>[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[N:6]=[C:7]([C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]([CH:30]=[O:31])=[CH:11][CH:10]=3)[NH:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 18426830HCID 18426830, compoundHCID 178418339Butyllithium

Product 1

HCID 18426789HCID 18426789, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5,6-dichloro-2-(4-bromo-1-naphthyl)benzimidazole (160 mg, 0.408 mmol) in tetrahydrofuran (6 mL) were added n-butyllithium (1.6 mol/L; 0.64 mL) and dimethylformamide (0.077 mL, 1.0 mmol) sequentially at −78° C. under nitrogen atmosphere, and the mixture was stirred for 15 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (2:1 hexane/ethyl acetate) to afford 5,6-dichloro-2-(4-formyl-1-naphthyl)benzimidazole (72 mg, 52%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d5447f7470c04c3fbe3583b06eb4b16a
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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