Potassium Carbonate → Methyl 3-methoxy-4-(6-nitrobenzimidazol-1-ylmethyl)benzoate

HRID 1723218Notes

Reaction equation

HRID 1723218 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:11][CH:10]=[N:9][C:8]=2[CH:12]=1)([O-:3])=[O:2].Br[CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[O:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:26][O:25][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:15]=1[CH2:14][N:9]1[C:8]2[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[N:11]=[CH:10]1)[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 178526486HCID 178526486, compound

Product 1

HCID 14763096Methyl 3-methoxy-4-(6-nitrobenzimidazol-1-ylmethyl)benzoateYield 26%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 6-nitrobenzimidazole (2.0 g.) and methyl 4-bromomethyl-3-methoxybenzoate (B) (3.5 g.) in methyl ethyl ketone (61 ml.) was treated with potassium carbonate (1.9 g.) and then heated under reflux for 24 hours. The solvent was then evaporated. The residue was extracted with ethyl acetate and inorganic material removed by filtration. The filtrate was evaporated. The resultant residue was purified by flash chromatography on a 6×30 cm. silica gel column using 1:1 v/v hexane:ethyl acetate as the eluent to give methyl 3-methoxy-4-(6-nitrobenzimidazol-1-ylmethyl)benzoate (K) (1.07 g., 26%): NMR: 3.9 (s,3H, OCH3), 4.0(s,3H, OCH3), 5.7(s,2H, NCH2), 7.4(d, IH, Ar), 7.8(d,1H, H4 -benzimidazole), 8.1(dd, 1H, H5 -benzimidazole), 8.6(br s,2H, H2,7 -benzimidazole).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent was then evaporated
  4. extractionThe residue was extracted with ethyl acetate and inorganic material
  5. customremoved by filtration
  6. customThe filtrate was evaporated
  7. customThe resultant residue was purified by flash chromatography on a 6×30 cm

Sources & evidence

ORD record
ord-db02119677a04ebc880d082b4d8c1aa2
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

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