N[C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:13].N([O-])=O.[Na+].[I-:18].[K+]>Cl.O.ClCCl>[I:18][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:13]
4-Amino-3,5,N-trimethyl-benzamide (850 mg, 4.77 mmol) is suspended in hydrochloric acid (37%, 2 mL), stirred until completely dissolved then cooled to 0° C. Sodium nitrite (494 mg, 7.15 mmol) in water (0.5 mL) is added and the mixture stirred for 1 hour at 0° C. Potassium iodide (2.38 g, 14.31 mmol) in 1.5 mL water is added and the mixture stirred for 15 minutes. The mixture is diluted with dichloromethane then washed with 10% aqueous sodium thosulfate solution, dried and the solvent removed under vacuum. The residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane) to give the title compound. (Yield 850 mg).
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