Methanol → HCID 57061118, compound

HRID 1034275Notes

Reaction equation

[H-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH:4]=1.Br[CH2:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1.CO>C1COCC1.C(OCC)(=O)C.O>[N:3]1([CH2:13][C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (80% dispersion in oil) (0.61 g, 0.02 mol) was added to a stirred solution of benzimidazole (2.00 g, 0.017 mol) in dry THF (30 ml) under argon. After 90 m the mixture was cooled to 0° C. and treated with ethyl 4-bromomethylbenzoate (4.50 g, 0.019 mol) dissolved in dry THF (20 ml). The mixture was allowed to warm to ambient temperature and stirred overnight. Methanol (1 ml) was added, followed by water and the product extracted using ethyl acetate (3×75 ml). The combined organic layers were washed with water (2×50 ml), dried over K2CO3 and the solvent removed to give the crude product (4.87 g). Flash chromatography (flash silica, ethyl acetate) gave, after crystallisation from toluene, ethyl 4-[1H-benzimidazylmethyl]benzoate (1.61 g, 34%) as a white crystalline solid.

Workup

temperatureto warm to ambient temperature
extractionthe product extracted
washThe combined organic layers were washed with water (2×50 ml)
dry with materialdried over K2CO3
customthe solvent removed
customto give the crude product (4.87 g)
customafter crystallisation from toluene, ethyl 4-[1H-benzimidazylmethyl]benzoate (1.61 g, 34%) as a white crystalline solid

Sources & evidence

ORD record: ord-fbe1008539414da2903d3a99f0528741
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05314880

Reaction notes

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