Methanol → 2-Nitro-4-(phenylmethanesulfinyl)aniline

Reaction equation

C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])=[CH:7][C:6]=1[N+:20]([O-:22])=[O:21])(=O)C.[OH-].[Na+].CO>O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])=[CH:7][C:6]=1[N+:20]([O-:22])=[O:21]

Participants

Procedure

2.42 G. 1-acetamido-2-nitro-4-benzylthiobenzene in 25 ml. chloroform is treated at -20 to -15° C with 1.6 g. 40% peracetic acid in 2 ml. methanol. The mixture is allowed to warm slowly to room temperature, held for 6 hours and washed with sodium bisulfite solution and sodium bicarbonate solution, dried and stripped. The residue is recrystallized from methanol giving 1-acetamido-2-nitro-4-benzylsulfinylbenzene. 2.14 G. 1-acetamido-2-nitro-4-benzylsulfinylbenzene is treated with 4 ml. 5N sodium hydroxide and 12 ml. methanol, on steam bath for 30 minutes, diluted with water, and filtered to give 1-amino-2-nitro-4-benzylsulfinylbenzene.