Sodium hydride → HCID 54152907, compound

HRID 1768647Notes

Reaction equation

HRID 1768647 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH3:13])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:17][C:18]1[CH:19]=[CH:20][C:21]2[C:27](=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:26]3[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=3[CH2:24][O:23][C:22]=2[CH:38]=1>CN(C=O)C.C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH3:13])[N:7]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]4[C:27](=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:26]5[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=5[CH2:24][O:23][C:22]=4[CH:38]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 219956454-Methyl-2-propyl-1H-benzimidazoleHCID 54542434HCID 54542434, compound

Product 1

HCID 54152907HCID 54152907, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

4-Methyl-2-propyl-1H-benzimidazole (464 mg) was dissolved in a mixture of 50 ml of DMF and 80 ml of toluene, and 106.4 mg of sodium hydride (60% oily) was added to the solution under ice cooling, followed by stirring for 30 minutes. To the mixture was added 732 mg of Compound 1-c, and the mixture was heated under reflux for 3 hours. After the solvent was distilled off under reduced pressure, the residue was diluted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate/triethylamine (20/5/1)] to give 629 mg (61%) of the product.

Workup

  1. additionwas added to the solution under ice cooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. additionthe residue was diluted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate/triethylamine (20/5/1)]

Sources & evidence

ORD record
ord-3f31b231969443c583662dc0ae47849f
Source dataset
uspto-grants-1995_01
Patent number
US05378701

Reaction notes

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