Sodium Hydroxide → 1H-Benzimidazole-6-carbonitrile

HRID 552834Notes

Reaction equation

HRID 552834 reaction equation
O=P(Cl)(Cl)Cl.[NH:6]1[C:10]2[CH:11]=[C:12]([C:15]([NH2:17])=O)[CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.[OH-].[Na+]>CN(C=O)C>[NH:6]1[C:10]2[CH:11]=[C:12]([C:15]#[N:17])[CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 154216421H-Benzimidazole-6-carboxamide

Product 1

HCID 2239061H-Benzimidazole-6-carbonitrileYield 27.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under ice-cooling, to DMF (30 ml) was slowly added dropwise POCl3 (6.68 g, 4.06 ml), followed by reaction at room temperature for 2 hours, and then a solution of 1H-benzimidazole-6-carboxamide (2.38 g) in DMF (47.6 ml) was added thereto, followed by stirring at room temperature for 2 hours. To the solution was added a 1M aqueous NaOH solution (pH 6 to 7), followed by stirring at room temperature for 0.5 hour. The solution was extracted with EtOAc, and the organic layer was combined, washed with saturated brine, dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. The residue was purified by silica gel chromatography, and powdered/washed with IPE to obtain 1H-benzimidazole-6-carbonitrile (0.58 g) as a pale red crystal.

Workup

  1. customfollowed by reaction at room temperature for 2 hours
  2. stirringby stirring at room temperature for 0.5 hour
  3. extractionThe solution was extracted with EtOAc
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by silica gel chromatography
  9. washpowdered/washed with IPE

Sources & evidence

ORD record
ord-24cb78b3f98f4fa7bec703cdc4c93c93
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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