Ethanol → HCID 19101525, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-Methanesulfonamidoanilino)acetophenone (5.0 g, 16.4 mmol), ethyl cyanoacetate (4.5 g, 39.4 mmol) and ammonium acetate (1.5 g, 19.5 mmol) were combined in a 100 mL round-bottomed flask equipped with a magnetic stir bar. The mixture was lowered into a pre-heated 140° C. oil bath, and became a stirrable melt within several minutes. Heating continued for 35 min during which time ethanol and water byproducts were observed boiling off, and a bright yellow solid formed amidst the dark supernatant. The reaction was removed from the heat and allowed to cool to 25° C. under vacuum. The crude material was stirred in ethanol (20 mL) for 30 min, then the product was collected by filtration, washed with more ethanol, and dried to yield 3.0 g (52%) as a bright yellow powder, m.p. 280° C. (dec). NMR and mass spectral data were consistent with the assigned structure. Elemental analysis: Calculated: C=61.18, H=4.28, N=11.89, S=9.07; Found: C=60.77, H=4.33, N=11.66, S=9.14.

Provenance & Evidence