[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=1.[N+:16]([C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25]Br)=[CH:21][CH:20]=1)([O-:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[N+:16]([C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25][N:2]([CH3:1])[CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][CH:10]=2)=[CH:21][CH:20]=1)([O-:18])=[O:17]A solution of N-methyl-4-methanesulphonamidophenethylamine (1.0 g) (see Preparation 8), 2-(4-nitrophenoxy)ethyl bromide (1.2 g) (C.A., 54, 11046a), potassium carbonate (0.67 g) and sodium iodide (0.72 g) in acetonitrile (100 ml) was stirred at reflux for 3 days. On evaporation to dryness, the residual oil was partitioned between water and methylene chloride. After two further extractions with methylene chloride, the organic portions were combined, washed with saturated brine solution, dried over anhydrous magnesium sulphate, filtered and evaporated to dryness. The resultant yellow oil was taken up in hot methanol, cooled and the title compound crystallised as a colourless solid, (1.2 g).
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