[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].CN(C=O)C.[H-].[Na+].Cl[CH2:20][O:21][CH2:22][CH3:23]>O>[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([S:11][CH2:20][O:21][CH2:22][CH3:23])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]A solution of 3.4 g of 2-nitro-5-mercaptoaniline in 20 ml. of DMF is treated with 0.5 g. of 100% sodium hydride, and 2.2 g. of chloromethyl-ethyl ether is added to the solution. After 30 minutes at 20-25° C, the solution is diluted with water and extracted with chloroform. Removal of the chloroform leaves 2-nitro-5-(ethoxymethylthio) aniline as an oil.
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