ChemicalBook CAS DataBase List N-Methoxy-N-methylacetamide

N-Methoxy-N-methylacetamide synthesis

7synthesis methods

Product Name:N-Methoxy-N-methylacetamide
CAS Number:78191-00-1
Molecular formula:C4H9NO2
Molecular Weight:103.12

N-Methoxy-N-methylacetamide can be prepared by reaction of Acetyl Chloride with commercially available N,O-Dimethylhydroxylamine hydrochloride in pyridine, followed by distillation at reduced pressure (65%).

6638-79-5 Synthesis

6638-79-5
587 suppliers
$6.00/25g

75-36-5 Synthesis

75-36-5
577 suppliers
$17.92/100G

78191-00-1
286 suppliers
$6.00/5g

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

123-86-4 Synthesis