Hydrochloric Acid → 3-Amino-3-(3-fluoro-4-methoxyphenyl)thioacrylamide

Participants

Reaction Steps

Add dioxane (65 mL) to 3-amino-3-(3-fluoro-4-methoxyphenyl)acrylonitrile (25.0 g, 130 mmol) and thioacetamide (19.5 g, 260 mmol); then add 4 N HCl in dioxane (650 mL, 2,600 mmol) and allow the reaction to stir 4-8 h until complete by TLC. Evaporate the reaction mixture to dryness; then add dioxane (200 mL); add slowly TEA (dried with K2CO3, 1000 mL); and then add satd K2CO3 (1000 mL) and extract with EtOAc (2000 mL). Dry the organic phase (K2CO3) and evaporate to afford 3-amino-3-(3-fluoro-4-methoxyphenyl)thioacrylamide. Yield: 98.5%. ES-MS: m/e 227.0 (m+1).

Provenance & Evidence