[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26]>C(O)CCC>[CH3:1][N:2]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1A mixture of freshly distilled N-methylaniline (116 g, 1.1 mol), potassium carbonate (175 g, 1.25 mol), sodium iodide (4 g, 0.025 mol), 2-[2-(2-chloroethoxy)ethoxy]ethanol (168 g, 1 mol), and 900 mL of butanol was heated at reflux for 72 hours under nitrogen with vigorous stirring. After cooling and filtration the butanol was evaporated at reduced pressure to leave a tan oil. The oil was fractionally distilled in vacuo, yielding 150 g (63%) as a colorless oil, bp 190°-191° C. (0.13 mm).
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