[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH2:13])=O)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1.CCCCCC.C(Cl)Cl>C1(C)C=CC=CC=1.C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH2:13])=[S:23])=[CH:4][CH:3]=1
To a solution of 4-(4-bromophenyl)butyramide (1.653 g, 6.827 mmol) in toluene (35 mL) was added Lawesson's reagent (1.381 g, 3.414 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-(4-bromophenyl) thiobutyramide as off-white needles (0.196 g): mp 104°-105° C. 1H NMR (DMSO-d6) 300 mHz δ9.33 (br s, 1H), 9.12 (br s, 1H), 7.44 (d, J=8.11 Hz, 2H), 7.14 (d, J=8.48 H z, 2H), 2.56-2.41 (m, 4H), 1.95-1.85 (m, 2H).
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