Chemical Properties
Colorless liquid
Uses
The chloroacetyl derivatives are microbicides for adhesives, cellulose foams, oil emulsions, cooling water, etc.
Synthesis
Step 1: Morpholine (1.00 mL, 11.5 mmol) and toluene (30 mL) were added to a dry three-necked flask equipped with a magnetic stirrer under nitrogen protection. Potassium carbonate (3.17 g, 22.9 mmol) was then added and stirred until completely dissolved. Chloroacetyl chloride (0.91 mL, 11.4 mmol) was slowly added dropwise under the cooling of an ice bath, and after completion of the dropwise addition, the ice bath was removed, the temperature was raised to 60 °C and the reaction was continuously stirred for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered to remove insoluble solids, and the solids were washed with a small amount of toluene. The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent to give N-chloroacetylmorpholine as a white solid (1.87 g, quantitative yield). The product was characterized by 1H-NMR (270 MHz, CDCl3): δ 3.51-3.54 (m, 2H), 3.62-3.65 (m, 2H), 3.68-3.74 (m, 4H), 4.07 (s, 2H).
References
[1] Patent: EP1650194, 2006, A1. Location in patent: Page/Page column 34
[2] Patent: WO2012/72019, 2012, A1. Location in patent: Page/Page column 71-72
[3] Molecules, 2015, vol. 20, # 11, p. 19984 - 20013
[4] Patent: WO2016/147144, 2016, A1. Location in patent: Page/Page column 222
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6660 - 6671
