HCID 21468845, compound → HCID 178442273, compound

HRID 743911Notes

Reaction equation

HRID 743911 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 1:1 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 1:1 ethylacetate/hexane

Sources & evidence

ORD record
ord-98f8c243120641818f0ccb949e6a46d4
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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