[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.[CH2:19]([N:22]=[C:23]=[S:24])[CH2:20][CH3:21]>C(OCCC)(=O)C>[I:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[NH:1][C:23](=[S:24])[N:22]([CH2:19][CH2:20][CH3:21])[C:4]2=[O:6]To a slurry of 2-amino-5-iodobenzoic acid (20 g, 0.076 mol) in n-propyl acetate (63 mL) was added triethylamine (11.6 mL, 0.0.84 mol) followed by n-propyl isothiocyanate (8.7 mL, 0.084 mol) at room temperature. The resulting solution was heated to reflux and the water generated was removed in a Dean Stark trap. After 4 h, the reaction mixture was cooled to room temperature and filtered. The wetcake was washed with fresh n-propyl acetate and dried at 60° C. under vacuum. In this manner, 21.4 g of the title compound was obtained as a light tan solid. See Step 1A for 1H NMR data, the UV spectrum matched that of the material made previously.
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