Potassium Carbonate → 4-Nitro-1-(pyridin-4-yl)methyl-1H-benzimidazole

HRID 503837Notes

Reaction equation

HRID 503837 reaction equation
[N+:1]([C:4]1[C:12]2[N:11]=[CH:10][NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>CN(C=O)C>[N+:1]([C:4]1[C:12]2[N:11]=[CH:10][N:9]([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 1609494-Nitrobenzimidazole

Product 1

HCID 594286314-Nitro-1-(pyridin-4-yl)methyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 500-mL round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet is charged with compound 3b (3.30 g, 30.6 mmol), potassium carbonate (8.95 g, 64.8 mmol), anhydrous DMF (200 mL) and 4-chloromethylpyridine hydrochloride (3.98 g, 24.3 mmol) and the mixture is then stirred under nitrogen for 24 h at ambient temperature. After such time the reaction is partitioned between water (200 mL) and ethyl acetate (200 mL). The aqueous layer is separated and extracted with ethyl acetate (6×250 mL). The combined organic extracts are dried with sodium sulfate, and the drying agent is filtered off. The filtrate is then concentrated under vacuum to give a brown solid, which is purified by column chromatography to afford compound 3c as a yellow solid.

Workup

  1. customA 500-mL round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. customAfter such time the reaction is partitioned between water (200 mL) and ethyl acetate (200 mL)
  3. customThe aqueous layer is separated
  4. extractionextracted with ethyl acetate (6×250 mL)
  5. dry with materialThe combined organic extracts are dried with sodium sulfate
  6. filtrationthe drying agent is filtered off
  7. concentrationThe filtrate is then concentrated under vacuum
  8. customto give a brown solid, which
  9. customis purified by column chromatography

Sources & evidence

ORD record
ord-c918527dc8004b3c900b8a787ee8dd87
Source dataset
uspto-grants-2010_08
Patent number
US07777040B2

Reaction notes

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