2-Imidazolidinone,1-(2-propynyl)-(9CI) synthesis
- Product Name:2-Imidazolidinone,1-(2-propynyl)-(9CI)
- CAS Number:131423-07-9
- Molecular formula:C6H8N2O
- Molecular Weight:124.14
1943-83-5
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Yield:131423-07-9 75.65%
Reaction Conditions:
with sodium hydride in tetrahydrofuran;mineral oil at 0 - 20; for 3 h;
Steps:
1-(prop-2-yn-1-yl)imidazolidin-2-one (2):
Chloro-2-isocyanatoethane 1 (100 g, 947.66 mmol) was added at 0 °C to a stirred solution of prop-2-yn-1-amine (propargyl amine, 57.42 g, 1.04 mol, 1.0 equiv) in THF (1000 mL). The solution was warmed to 20°C and NaH (39.80 g, 995.05 mmol, 60% purity, 0.99 equiv) was added, the mixture was stirred for 3 hr. TLC indicated prop-2-yn-1-amine was consumed completely and one new spot formed. The reaction was quenched with acetic acid (50.0 mL), the THF was removed under reduced pressure, and the residue was diluted with water 400 mL and extracted with ethyl acetate 900 mL (300 mL x 3). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by crystallization from ethyl acetate/hexane to give 1-(prop-2-yn-1-yl)imidazolidin-2-one (2) as a white solid (89 g, 75.65% yield).
References:
WO2021/237223,2021,A1 Location in patent:Paragraph 00726
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