N-Methoxy-N-methylacetamide synthesis
- Product Name:N-Methoxy-N-methylacetamide
- CAS Number:78191-00-1
- Molecular formula:C4H9NO2
- Molecular Weight:103.12
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Yield:78191-00-1 78%
Reaction Conditions:
Stage #1: N,O-dimethylhydroxylamine*hydrochloridewith triethylamine in dichloromethane at 0; for 0.166667 h;Inert atmosphere;
Stage #2: acetyl chloride in dichloromethane at 0 - 22;
Steps:
N-Methoxy-N-methylacetamide (2a)
To a mixture of N-methoxymethylamine hydrochloride(1.367 g, 14.015 mmol) in DCM (30 mL) was slowly added TEA (2.836 g, 3.9 mL, 28.030mmol) at 0 oC and it was stirred for 10 min. Then acetyl chloride (1.1 g, 1.0 mL, 14.105 mmol)was added dropwise to the reaction mixture at 0 oC and it was stirred at 22 oC overnight. After the reaction mixture was quenched with sat. NaHCO3 solution, biphasic solution was separated and aqueous layer was extracted with DCM (2 X 30 mL). The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue afforded the desired product (1.12 g, 10.861 mmol, 78%) as a colorless liquid without further purification. 1H NMR (400 MHz, CDCl3) δ 3.65 (s, 3H), 3.13 (s, 3H), 2.08 (s, 3H); 13C NMR(100 MHz, CDCl3) δ 172.0, 61.1, 32.0, 19.8.
References:
Gim, Hyo Jin;Jung, Michael E. [Synthesis,2019,vol. 51,# 12,p. 2548 - 2552] Location in patent:supporting information
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