Hydrochloric Acid → N-Acetyl-N-methylglycine
Reaction equation
[NH:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2].C(N(CC)CC)C.[C:14](Cl)(=[O:16])[CH3:15].Cl>CN(C)C1C=CN=CC=1.O.O1CCOCC1.O1CCOCC1>[C:14]([N:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2])(=[O:16])[CH3:15]Participants
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- extractionThe mixture was extracted three times with ethyl acetate
- washThe extracts were washed with a saturated NaCl solution
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was crystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-7fea6619fe474223a060794c2cfbcd42
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05300492
Reaction notes
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