[Cl-].[NH4+].[OH2:3].[CH3:4][N:5]([CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)[S:6]([CH3:9])(=[O:8])=[O:7].C([OH:24])C>[Zn]>[S:6]([OH:8])([OH:24])(=[O:7])=[O:3].[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([NH:12][CH2:11][CH2:10][N:5]([CH3:4])[S:6]([CH3:9])(=[O:8])=[O:7])=[CH:18][CH:17]=1
A mixture of zinc powder (25 g), ammonium chloride (1.1 g), water (11.2 mL), and 96% ethanol (67.5 mL) was brought to reflux in a boiling water bath. N-methyl-N-[2-(4-nitrophenylamino)ethyl]methanesulfonamide (23) (12.3 g, 0.045 mol) was added in portions and heating was continued until the reaction medium decolorized. The resulting mixture was filtered while boiling and the filtrate was recovered onto 3.8 mL of 96% sulfuric acid. The zinc was washed with ethanol, the filtrate was cooled in ice, and the precipitate that formed was filtered off by suction. After recrystallization from 30 mL of ethanol and 30 mL of water, 14.4 g of product were isolated. A second recrystallization from 45 mL of 50% ethanol gave 11.5 g of expected product having the following elemental analyses:
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