Sodium hydride → HCID 66628264, compound

HRID 1471213Notes

Reaction equation

HRID 1471213 reaction equation
[CH2:1]([C:11]1[NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[N:12]=1)[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[H-].[Na+].I[CH2:23][CH2:24][CH3:25]>CN(C)C=O>[CH:1]([C:2]1[N:6]([CH2:5][CH2:4][CH3:10])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1)([C:11]1[N:12]([CH2:2][CH2:1][CH3:11])[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 2609682,2'-methylenebis(1h-benzimidazole)

Product 1

HCID 66628264HCID 66628264, compoundYield 151%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 0.79 g 2,2′-methylenebis(1H-benzimidazole) and 20 ml N,N-dimethylformamide under nitrogen. 0.42 g sodium hydride were added in portions and the mixture was stirred 20 minutes. 1.74 g 1-iodopropane were added slowly and the mixture was stirred at 22 C for 16 hrs. After quenching with the slow addition of 40 ml water, the product was extracted with ethyl acetate and washed with water. Solvent removal resulted in an oil which was purified by silica gel chromatography using 25% ethyl acetate in hexane to give 0.9 g of a light yellow oil which crystallized on standing.

Workup

  1. stirringthe mixture was stirred at 22 C for 16 hrs
  2. customAfter quenching with the slow addition of 40 ml water
  3. extractionthe product was extracted with ethyl acetate
  4. washwashed with water
  5. customSolvent removal
  6. customresulted in an oil which
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-3cb9e1b965264bcbaa3e1668ad8c7687
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

Loading…