Sodium hydride → HCID 19811372, compound

HRID 373076Notes

Reaction equation

HRID 373076 reaction equation
[C:1]([C:9]1[CH:27]=[CH:26][C:12]2[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:14](=[O:16])[NH:15][C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl.Cl[CH2:32][CH2:33][N:34]([CH3:36])[CH3:35]>CS(C)=O.O>[C:1]([C:9]1[CH:27]=[CH:26][C:12]2[N:13]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[C:14](=[O:16])[N:15]([CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 19811358HCID 19811358, compound

Product 1

HCID 19811372HCID 19811372, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 1.09 g of 5-benzoyl-1-(4-methoxybenzyl)-2H-benzimidazol-2-one in 10 ml of dimethylsulfoxide was added at room temperature 0.27 g of 60% dispersion of sodium hydride in mineral oil. After being stirred for 30 minutes, the reaction mixture was treated with 0.48 g of chloroethyldimethylamine hydrochloride at room temperature for 2 hours and at 55° C for 3 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate layer was extracted with 10% hydrogen chloride. The aqueous layer was alkalized with 20% sodium hydroxide and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine in turn and dried over anhydrous sodium sulfate. After removal of the solvent in vacuo, the residue was chromatographed on silica gel using chloroform-methanol (15:1) to afford 1.14 g of 5-benzoyl-1,3-dihydro-3-(2-dimethylaminoethyl)-1-(4-methoxybenzyl)-2H-benzimidazol-2-one.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate layer was extracted with 10% hydrogen chloride
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water and brine in turn
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removal of the solvent in vacuo
  7. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-7fa5a8c7d7ed475d8e82488ebd197604
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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