Potassium Iodide → 1-(2,4-Dichlorobenzyl)-4-ethoxycarbonyl-2-methylbenzimidazole

HRID 276068Notes

Reaction equation

HRID 276068 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[NH:13][C:12]([CH3:15])=[N:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2].[Cl:16][C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[CH2:19]Cl.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:16][C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[CH2:19][N:11]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:14]=2[N:13]=[C:12]1[CH3:15]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 72122,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 18680979ethyl 2-methyl-1H-benzimidazole-4-carboxylate

Product 1

HCID 186810891-(2,4-Dichlorobenzyl)-4-ethoxycarbonyl-2-methylbenzimidazoleYield 25.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.61 g of 4-ethoxycarbonyl-2-methylbenzimidazole, 3.08 g of 2,4-dichlorobenzyl chloride, 1.51 g of potassium iodide, 1.05 g of potassium carbonate and 4 ml of N,N-dimethylformamide was stirred at 80° C. for 16 hours. The reaction mixture was extracted with chloroform and with water. The chloroform layer was washed with water, dried, and concentrated. The residue was purified through silica-gel column chromatography (eluent: a mixture of hexane and ethyl acetate at a ratio of 2:8) to give 0.730 g of 1-(2,4-dichlorobenzyl)-4-ethoxycarbonyl-2-methylbenzimidazole (297).

Workup

  1. extractionThe reaction mixture was extracted with chloroform and with water
  2. washThe chloroform layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified through silica-gel column chromatography (eluent
  6. additiona mixture of hexane and ethyl acetate at a ratio of 2:8)

Sources & evidence

ORD record
ord-03f3532da7084458901a2f2a057bfb80
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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