Water → HCID 11543588, compound
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]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- stirringthe resulting mixture was stirred at −78° C. for an addition ½ hour
- stirringAfter stirring at 0° C. for 6 hrs
- extractionthe resulting solution was extracted with EtOAc
- washthe organic layer was washed with brine
- dry with materialdried over anhydrous Na2SO4
- distillationSolvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-a32755a5c142422b9dfd6be821785465
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879895B2
Reaction notes
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