HCID 21468845, compound → HCID 178442273, compound

HRID 1938630Notes

Reaction equation

HRID 1938630 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[NH2:8]>C(O)C>[C:11]([C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=1[C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:4]([CH2:3][CH2:2][CH2:7][CH2:6][CH3:5])=[N:1][C:2]=2[CH:3]=1)#[N:12]

Participants

3

Reactant 1

HCID 21468845HCID 21468845, compound

Product 1

HCID 178442273HCID 178442273, compoundYield 160.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(3,4-Diaminophenyl)benzonitrile (4.3 mmoles, 0.9 g) and ethyl hexanoamidate hydrochloride were dissolved in 20 ml ethanol and stirred for 2.5 hours. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate and washed with water, saturated NaHCO3 and brine. The organic phase was dried and concentrated. The residue was chromatographed on silica gel eluted with 1: ethylacetate/hexane to yield 1.0 g of 5-(2-Cyanophenyl)-2-pentyl-1H-benzimidazole.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water, saturated NaHCO3 and brine
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel
  7. washeluted with 1

Sources & evidence

ORD record
ord-b273ebee56c649bf959eab472e8cd812
Source dataset
uspto-grants-1997_12
Patent number
US05693633

Reaction notes

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