Water → HCID 11543588, compound

HRID 1394463Notes

Reaction equation

HRID 1394463 reaction equation
C[C:2]#[N:3].[CH2:4]([Li])CCC.[Cl:9][C:10]1[C:21]([Cl:22])=[CH:20][C:13]2[NH:14][C:15]([C:17](=[O:19])[CH3:18])=[N:16][C:12]=2[CH:11]=1.O>C1COCC1>[Cl:22][C:21]1[C:10]([Cl:9])=[CH:11][C:12]2[NH:16][C:15]([C:17]([OH:19])([CH3:4])[CH2:18][C:2]#[N:3])=[N:14][C:13]=2[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 534071411-(5,6-Dichloro-1H-benzimidazol-2-yl)ethan-1-oneHCID 178418339Butyllithium

Product 1

HCID 11543588HCID 11543588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

CH3CN was added to a solution of n-butyl lithium in THF (8 ml) at −78° C. and the mixture was stirred at −78° C. for 45 minutes. To this solution was added 1-(5,6-dichloro-1H-benzimidazol-2-yl)-ethanone in THF (6 ml) and the resulting mixture was stirred at −78° C. for an addition ½ hour. After stirring at 0° C. for 6 hrs, water was added, the resulting solution was extracted with EtOAc, the organic layer was washed with brine and then dried over anhydrous Na2SO4. Solvent was distilled off under reduced pressure. Column chromatography (silica gel, EtOAc/hexanes 10% to 50%) yielded the title product as an off-white solid.

Workup

  1. stirringthe resulting mixture was stirred at −78° C. for an addition ½ hour
  2. stirringAfter stirring at 0° C. for 6 hrs
  3. extractionthe resulting solution was extracted with EtOAc
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. distillationSolvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4169212c7e0c451eae12d54e5041e301
Source dataset
uspto-grants-2008_03
Patent number
US07348438B2

Reaction notes

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