1,1'-Carbonyldiimidazole → 2-cyclopropyl-N-methoxy-N-methylacetamide

To a solution of 2-cyclopropylacetic acid (C62) (30 g, 300 mmol) in dichloromethane (800 mL) was added 1,1′-carbonyldiimidazole (54 g, 333 mmol) portion-wise, not allowing the temperature to exceed 25° C. The mixture was stirred at room temperature for 2 hours. N,O-Dimethylhydroxylamine hydrochloride (30 g, 308 mmol) was added in one portion and stirred at room temperature for 18 hours. The mixture was washed with water (2×200 mL) and saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate and concentrated to give crude product as a yellow oil, which was directly used in the next step. Yield: 48 g, 336 mmol, 112%. 1H NMR (400 MHz, CDCl3) δ 3.62 (s, 3H), 3.12 (s, 3H), 2.30 (d, J=7.2 Hz, 2H), 1.03-1.06 (m, 1H), 0.48-0.52 (m, 2H), 0.11-0.13 (m, 2H).

1. customto exceed 25° C
2. stirringstirred at room temperature for 18 hours
3. washThe mixture was washed with water (2×200 mL) and saturated aqueous sodium chloride solution (100 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customto give crude product as a yellow oil, which

ORD record

ord-2a552bf364b24f0e82cbf9ad48541559

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403846B2