Quinone → HCID 178509507, compound

HRID 1858028Notes

Reaction equation

HRID 1858028 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[NH2:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[NH2:18])[C:13]#[N:14].C1(=O)C=CC(=O)C=C1>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:18][C:17]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 4650QuinoneHCID 142732-PyridinecarboxaldehydeHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 178509507HCID 178509507, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 2-pyridinecarboxaldehyde (212 mg, 1.98 mmol, 1 eq), 3,4-diaminobenzonitrile (263 mg, 1.98 mmol, 1 eq) and ethanol (20 mL) was stirred at ambient temperature under nitrogen for 5 to 10 minutes and then 1,4-benzoquinone (233 mg, 2.16 mmol, 1.2 eq) was added. The mixture was heated at reflux for 3 hours and then concentrated. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was separated, dried (MgSO4), filtered and concentrating to dryness to provide 2-pyridin-2-yl-1H-benzimidazole-5-carbonitrile (348 mg, 1.58 mmol) as an off white solid; ESI LC/MS: 261.9=(MH+ +CH3CN); 1H-NMR (300 Mhz, DMSO-d6): 7.65-7.755 (m, 2H), 7.769 (d, 1H), 8.060 (t, 1H), 8.163 (s, 1H), 8.395 (d, 1H), 8.772 (d, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated
  4. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrating to dryness

Sources & evidence

ORD record
ord-b1760ffd98cf4fa4ac0c961e7a14629c
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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