Ethanolamine → HCID 18185419, compound

Participants

Reaction Steps

2-(1,1-dimethyl-2-chloroethyl)-2-oxazoline was prepared as follows. Initially, N-(2-hydroxyethyl)-3-chloropivalamide was prepared by adding dropwise, at room temperature, a solution of 3-chloropivaloyl chloride (1.0 eq., 22.4 g, 0.14 mol) in CH2Cl2(100 mL) to a stirred mixture of 2-aminoethanol (2.0 eq., 17.6 g, 0.29 mol) in CH2Cl2(300 mL) over a period of one (1) hour. This mixture was allowed to auto-reflux for twenty (20) minutes and was then stirred for an additional forty (40) minutes. The whitish-yellow precipitate that formed was gravity filtered, and the resulting yellow solution was concentrated under vacuum. The resulting viscous yellow oil (23 g, 89% yield) was pure N-(2-hydroxyethyl)-3-chloropivalamide, as evidenced by 1H NMR (CDCl3): δ1.31 (s, 6H, CH3, CH3), 3.44 (q, 2H, CH2—NH), 3.61 (s, 2H, CH2—Cl), 3.73 (t, 2H, CH2—OH), 6.3 (br s, 1H, NH).

Provenance & Evidence