Benzylamine → N-benzyl-3-methylfuran-2-carboxamide

To a mixture of 3-methylfuran-2-carboxylic acid (0.79 g, 6.28 mmol), 1-hydroxybenzotriazole (1.27 g, 9.42 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.81 g, 9.42 mmol) in N,N-dimethylformamide (6 mL) was added N,N-diisopropylethylamine (3.30 mL, 18.94 mmol) and benzylamine (0.69 mL, 6.28 mmol). The reaction mixture was stirred for 16 hours, and then diluted with ethyl acetate (75 mL). The organic layer was washed with 10% aqueous hydrochloric acid (2×25 mL), saturated aqueous sodium bicarbonate (2×25 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford N-benzyl-3-methylfuran-2-carboxamide as a light brown solid (0.57 g, 80%): 1H NMR (300 MHz, CDCl3) δ 7.37-7.28 (m, 5H), 7.27 (d, J=1.5 Hz, 1H), 6.61 (br s, 1H), 6.34 (d, J=1.5 Hz, 1H), 4.59 (d, J=5.9 Hz, 2H), 2.42 (s, 3H); MS (ES+) m/z 216.2 (M+1).

1. washThe organic layer was washed with 10% aqueous hydrochloric acid (2×25 mL), saturated aqueous sodium bicarbonate (2×25 mL)
2. dry with materialdried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo

ORD record

ord-a27f6d3053db470ab6c0a068ba082a3f

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501746B2