HCID 21468845, compound → HCID 178442273, compound

HRID 866284Notes

Reaction equation

HRID 866284 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-9e2989d849a94016b0fecb395bdac2e2
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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