Benzimidazole → HCID 36355606, compound

HRID 2411200Notes

Reaction equation

HRID 2411200 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N:13]1([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

Participants

6

Reactant 4

HCID 5798BenzimidazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 36355606HCID 36355606, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 6-chloronicotinate (2.43 g), 1H-benzimidazole (1.7 g) and potassium carbonate (5.43 g) was added N,N-dimethylformamide (20 mL), and the mixture was stirred at 50° C.-60° C. for 9 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (2.28 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. customThe obtained residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-283d154e8f3544c0a3c5f0e65ddd0111
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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