Methylamine → HCID 46932331, compound

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (0.102 g, 0.86 mmol) was added to a suspension of 5-(2,3-dichlorophenylsulfanyl)-4-nitrothiophene-2-carboxylic acid (0.15 g, 0.43 mmol) in toluene (5 mL) and the stirred mixture was heated at 80° C. for 1 hour. TLC analysis showed no acid remaining so the mixture was allowed to cool to ambient temperature and then concentrated in vacuo to give the dark brown viscous oil. The oil was dissolved in 1,4-dioxane (1 mL) and added at 5° C. to stirred 40% aqueous methylamine solution (5 mL). The mixture was stirred for 15 minutes then the resulting solid was collected by filtration, washed with water (3×1 mL) and dried in vacuo at 40° C. overnight to afford the title product as a beige solid (55 mg, 35% yield). 1H NMR (CDCl3) δ: 7.84 (1H, s) 7.70 (2H, m), 7.36 (1H, m), 6.01 (1H, broad s), 2.95 (3H, d, J=4.9 Hz).

Provenance & Evidence