Imidazole → 1-{4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzoyl}imidazole

HRID 430026Notes

Reaction equation

HRID 430026 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][C:10]([NH:12][CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=2)=[O:11])[CH:3]=1.[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1>O1CCCC1>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][C:10]([NH:12][CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([N:23]3[CH:27]=[CH:26][N:25]=[CH:24]3)=[O:19])=[CH:16][CH:15]=2)=[O:11])[CH:3]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 45358729HCID 45358729, compound

Product 1

HCID 98191321-{4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzoyl}imidazoleYield 55.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g (2.9 mmole) of 4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzoyl chloride hydrochloride was added to a tetrahydrofuran (10 ml) solution including 0.6 g (8.8 mmole) of imidazole, followed by stirring for 1 hour. A deposited imidazole hydrochloride was removed by filtration, and the reaction solution was then concentrated. Ethyl acetate and water were added to the solution to carry out partition, and the organic layer was then treated in an ordinary manner to obtain 0.54 g (yield: 55%) of 1-{4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzoyl}imidazole.

Workup

  1. customA deposited imidazole hydrochloride was removed by filtration
  2. concentrationthe reaction solution was then concentrated
  3. additionEthyl acetate and water were added to the solution
  4. customto carry out partition
  5. additionthe organic layer was then treated in an ordinary manner

Sources & evidence

ORD record
ord-2af7bd0a26914cfe849a76bd1132a9de
Source dataset
uspto-grants-2001_11
Patent number
US06320078B1

Reaction notes

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