2-Methoxyethylamine → N-(2-methoxyethyl)acrylamide

N,N-Diisopropylethylamine (3.21 g, 25 mmol) was added to a stirred, ice-cooled solution of acryloyl chloride (2.25 g, 25 mmol) in dichloromethane (30 ml) under nitrogen followed, 2 minutes later, by 2-methoxyethylamine (1.92 g, 25.6 mmol) added dropwise over 1 hour. The cooling bath was removed, then the reaction mixture stirred for 18 hours at room temperature and washed twice with water. The combined aqueous washings were saturated with sodium chloride and exhaustively extracted with dichloromethane. All the dichloromethane solutions were combined, washed twice with 2M aqueous sodium carbonate solution, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a solvent gradient of ethanol: dichloromethane (0:100 to 5:95), to yield the required amide as an oil. Rf 0.63 (SS 7). Found: C,54.97; H,9.24; N,10.68. C6H11NO2 ; 0.10 H2O requires C,55.04; H,8.62; N,10.70%. LRMS: m/z 130.4 (M+1)+.

1. customThe cooling bath was removed
2. washwashed twice with water
3. extractionexhaustively extracted with dichloromethane
4. washwashed twice with 2M aqueous sodium carbonate solution
5. dry with materialdried (Na2SO4)
6. customevaporated under reduced pressure
7. customThe residue was purified by column chromatography on silica gel
8. washeluting with a solvent gradient of ethanol: dichloromethane (0:100 to 5:95)

ORD record

ord-3c615f93ffa0409b87e1e3dc96dbe455

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05607960