Benzimidazole → methyl 3-(1H-benzo[d]imidazol-1-yl)propanoate

HRID 52829Notes

Reaction equation

HRID 52829 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12]>C1CCN2C(=NCCC2)CC1.O1CCCC1>[N:1]1([CH2:12][CH2:11][C:10]([O:14][CH3:15])=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 5798BenzimidazoleHCID 7294Methyl Acrylate

Product 1

HCID 10536181methyl 3-(1H-benzo[d]imidazol-1-yl)propanoateYield 91.5%

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.0 g (84 mmol) of benzimidazole, 22.7 ml (250 mmol) of methyl acrylate and 3 drops of DBU in 50 ml of tetrahydrofuran was heated at reflux for 2 days. The resulting solution was concentrated in vacuo, and the residue was purified by silica gel chromatography using 3% methanol in chloroform to provide 15.7 g (92%) of the desired compound (Rf 0.58, 10% methanol in chloroform).

Workup

  1. temperatureat reflux for 2 days
  2. concentrationThe resulting solution was concentrated in vacuo
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fc911843eb184d8ca662e4b393eb00f1
Source dataset
uspto-grants-1997_04
Patent number
US05616714

Reaction notes

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