Hydrochloric Acid → N-Acetyl-N-methylglycine

Participants

Reaction Conditions

Reaction Steps

4-Dimethylaminopyridine (3.66 g) was added to a solution of sarcosine (26.7 g) and triethylamine (50 ml) in (1:1) dioxane water (150 ml) cooled at 0° C. A solution of acetyl chloride (22.37 ml) in dioxane (20 ml) was added dropwise over a period of 30 min. The reaction solution was then stirred at room temperature for 1 hour and subsequently was acidified to pH 3 with cold 50% aqueous HCl. The mixture was extracted three times with ethyl acetate. The extracts were washed with a saturated NaCl solution, dried over Na2SO4 and concentrated. The residue was crystallized from ethyl acetate to give N-acetyl-sarcosine, m.p. 135°-137° C. Fab Mass spec. m/e 132 (M+H); Anal. for C5H9NO3, Calcd: C, 45.79; H, 6.91; N, 10.68; Found: C, 45.78; H, 7.03; N, 10.64.

Provenance & Evidence