Synthesis of a Weinreb amide.; N,N’-Dimethoxy-N,N’-dimethylsuccinamide.
Submitted Nov 02, 2015, published Nov 11, 2015
N,O-dimethylhydroxylamine hydrochloride (TCI Chemicals)
Succinyl chloride (ACROS)
Triethylamine (Fisher Chemical)
Dichloromethane (Fisher Chemical)
In a three-necked round bottomed flask fitted with an argon inlet, a thermometer and an addition funnel, are successively placed N,O-dimethylhydroxylamine hydrochloride (24.00 g), dichloromethane (270 mL) and succinyl chloride (12.9 mL). The resulting suspension is cooled to 0°C under argon and triethylamine (67 mL) is added dropwise at such a rate that internal temperature remains below 10°C. When addition is completed, reaction mixture is stirred at 0°C for two hours. The solution is then allowed to warm to room temperature and then poured onto saturated aqueous sodium bicarbonate solution (150 mL). The obtained slurry is filtered on a glass sintered funnel and the layers are separated. Aqueous layer is extracted with dichloromethane (2×75 mL). Organic layers are combined, washed with brine (50 mL), dried over anhydrous sodium sulphate and concentrated. The compound is obtained as a light brown solid (15.31 g; 64%)
1H NMR (300 MHz, CDCl3) ppm = 3.73 (6H, s); 3.17 (6H, s); 2.76 (4H, s).13C NMR (75 MHz, CDCl3) ppm = 173.3; 61.1; 32.1; 26.3.
Harding, M. et al. J. Chem. Soc., Perkin Trans. 1, 2002, 2403-2413.
1 H NMR spectra (JH_258_1(H).pdf)
13 C NMR spectra (JH_258_1(C).pdf)
e.g. Actual NMR spectra (as images or jdx files for interactive spectra), photographs of apparatus, TLC’s or crystals or videos. Please contact the ChemSpider team (ChemSpider-at-rsc.org) for help with this.
Keywords: amides, nucleophilic, substitution