Potassium Carbonate → HCID 57924561, compound

HRID 553456Notes

Reaction equation

HRID 553456 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>CN(C=O)C>[Cl:1][C:2]1[N:6]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73784IodocyclopentaneHCID 785722-Chlorobenzimidazole

Product 1

HCID 57924561HCID 57924561, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-1H-benzo[d]imidazole (152 mg, 1.0 mmol.) in DMF was added K2CO3 (277 mg, 2.0 mmol.) and iodocyclopentane (295 mg, 1.5 mmol.). The reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into ice-water. The mixture was extracted with ethyl acetate (30 mL×3), washed with brine, dried over Na2SO4, concentrated to give a residue, which was purified by column chromatography to afford 2-chloro-1-cyclopentyl-1H-benzo[d]imidazole (130 mg, 59%). 1H NMR (400 MHz, CDCl3) δ 7.68˜7.60 (m, 1 H), 7.39˜7.30 (m, 1 H), 7.20˜7.15 (m, 2 H), 5.04˜4.90 (m, 1 H), 2.25˜1.92 (m, 6 H), 1.85˜1.70 (m, 2 H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (30 mL×3)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give a residue, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c14d7266e68a4241bbdea1ce70a6b74d
Source dataset
uspto-grants-2011_11
Patent number
US08048862B2

Reaction notes

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