4-phenylbutanamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-phenylbutyramide (0.373 g, 2.28 mmol) in toluene (15 mL) was added Lawesson's reagent (0.461 g, 1.14 mmol). The reaction was refluxed overnight, cooled to room temperature and concentrated yielding an orange oil. Flash chromatography of this oil (1:1 hexane:methylene chloride with 1% acetic acid) yielded 4-phenylthiobutyramide (0.184 g) as a white solid: 1HNMR (DMSO d6 ) 400 mHz 9.33 (s, 1 H), 9.13 (s, 1 H), 7.29-7.23 (m, 2 H), 7.20-7.15 (m, 3 H), 2.56 (t, J=7.58 Hz, 2 H), 2.50-2.42 (m, 2 H), 2.00-1.85 (m, 2 H). The reaction was refluxed overnight concentrated yielding an orange oil