Sodium hydride → 1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-2-chloro-1H-benzimidazole

HRID 1584432Notes

Reaction equation

HRID 1584432 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].Cl[CH2:14][C:15]1[O:16][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:19]=1>CN(C)C=O.O>[Cl:1][C:2]1[N:6]([CH2:14][C:15]2[O:16][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:19]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 785722-ChlorobenzimidazoleHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

Product 1

HCID 184649721-(5-(ethoxycarbonyl)fur-2-ylmethyl)-2-chloro-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Combine 2-chlorobenzimidazole (10.0 g, 66 mmol), and dimethylformamide (100 mL). Add portionwise sodium hydride (1.63 g, 68 mmol). After the evolution of gas ceases, add a solution of ethyl 2-chloromethyl-5-furoate (12.45 g, 0.66 mmol) in dimethylformamide (20 mL). After 18 hours, dilute the reaction mixture with water and extract four times with diethyl ether. Combine the organic layers and extract with water and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue eluting with 5% methanol/0.2% concentrated aqueous ammonia solution/dichloromethane to give 2-chloro-1-(5-ethyoxycarbonylfur-2-ylmethyl)-1H-benzimidazole.

Workup

  1. extractionextract four times with diethyl ether
  2. extractionextract with water
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue
  7. washChromatograph the residue eluting with 5% methanol/0.2% concentrated aqueous ammonia solution/dichloromethane

Sources & evidence

ORD record
ord-59e06e3e36f04e128e23607b85ea5265
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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