Benzamidine → 4-Dimethoxymethyl-2-phenyl-1H-imidazole

HRID 1643227Notes

Reaction equation

[C:1]([NH2:9])(=[NH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18](=O)[CH:19]([O:22][CH3:23])[O:20][CH3:21].C(OCC)(=O)C>CN(C=O)C.O>[CH3:21][O:20][CH:19]([O:22][CH3:23])[C:18]1[N:8]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:9][CH:17]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of benzamidine 207 (1.44 g, 12 mmol) and potassium carbonate (4.1 g, 30 mmol) in anhydrous DMF (25 mL) is slowly added a solution of 3-bromo-1,1-dimethoxy-propan-2-one 206 (1.97 g, 10 mmol) in anhydrous DMF (10 mL) over 30 min. The mixture is then heated at 50-60° C. for 2 h. After cooling to room temperature, ethyl acetate (100 mL) and water (100 mL) were added. The organic phase is separated and the aqueous phase is extracted with ethyl acetate twice and the combined organic phase is washed with water (3×20 mL) and brine. Removal of solvents under reduced pressure and purification of the residue by column chromatography affords the desired product as a white solid. Yield: 2.08 g; LC-MS (MH+): 219. 1H NMR (300 MHz, CDCl3) δ 7.88-7.85 (m, 2H), 7.37-7.46 (m, 4H), 5.49 (s, 1H), 3.36 (s, 6H).

Workup

temperatureAfter cooling to room temperature
customThe organic phase is separated
extractionthe aqueous phase is extracted with ethyl acetate twice
washthe combined organic phase is washed with water (3×20 mL) and brine
customRemoval of solvents
customunder reduced pressure and purification of the residue by column chromatography

Sources & evidence

ORD record: ord-2f957bba880948e5b1c3993dc32b049e
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119665B2

Reaction notes

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