Sodium hydride → HCID 66627876, compound

HRID 1471292Notes

Reaction equation

HRID 1471292 reaction equation
[C:1]1([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=1.[H-].[Na+]>CN(C)C=O>[C:2]1([C:7]2[N:11]([CH2:12][CH2:10][CH2:9][CH2:15][CH3:14])[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:16]1[N:17]([CH2:3][CH2:2][CH2:1][CH2:6][CH3:5])[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 828108HCID 828108, compound

Product 1

HCID 66627876HCID 66627876, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 1.5 g of 2,2′-(1,2-phenylene)bis(1H-benzimidazole) and 30 ml of N,N-dimethylformamide, and the mixture was cooled to 5 C. To this mixture was added 0.48 g of 60% sodium hydride in mineral oil in small portions, and after stirring at 5-10 C for 30 minutes, 2.4 g of 1-1-iodopentane were added. The reaction mixture was warmed to 22 C for and stirred for 16 hours, then quenched with 50 ml water. The product was extracted with 40 ml ethyl acetate and following removal of the solvent, the product was purified by silica gel chromatography using 25% ethyl acetate, 75% hexane and 0.1% triethylamine resulting in 2.1 g of a yellow solid.

Workup

  1. temperaturethe mixture was cooled to 5 C
  2. temperatureThe reaction mixture was warmed to 22 C for and
  3. stirringstirred for 16 hours
  4. customquenched with 50 ml water
  5. extractionThe product was extracted with 40 ml ethyl acetate
  6. customremoval of the solvent
  7. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-112f41877efe4824b2860d349669a7b8
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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