Propynoic acid amide

Chemical Properties

Waxy Yellow Solid

Uses

Propiolamide (cas# 7341-96-0) is a compound useful in organic synthesis.

Definition

ChEBI: Propynamide is a ynamide, a terminal acetylenic compound and a primary carboxamide. It is functionally related to a propynoic acid.

Synthesis

General procedure for the synthesis of propargylamide from methyl propargylate: 1. Synthesis of propargylamide: Methyl propargylate (25 mL, 281 mmol) was slowly added dropwise to concentrated ammonia (25 mL, 281 mmol) at 30 °C. The reaction mixture was stirred at -30 °C for 20 min. Subsequently, the solvent was removed by distillation under reduced pressure. Ether (200 mL) was added to the residue, the mixture was filtered and the filtrate was concentrated to afford the target product propargylamide (18.5 g, 95.4% yield) as a solid. The product was characterized by 1H-NMR (DMSO-d6): δ 4.08 (1H, s), 7.62 (1H, br s), 8.08 (1H, br s).

References

[1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 360 - 367
[2] Tetrahedron, 2004, vol. 60, # 31, p. 6665 - 6677
[3] Patent: EP1813606, 2007, A1. Location in patent: Page/Page column 88
[4] Journal of the American Chemical Society, 2001, vol. 123, # 49, p. 12353 - 12363
[5] Patent: EP1007509, 2004, B1. Location in patent: Page 6-7