Sodium Carbonate → 2,4-Bis(hydroxyethylsulfonylmethyl)aniline

Reaction equation

[OH:1][CH2:2][CH2:3][S:4]([CH2:7][C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH2:18][CH2:19][OH:20])(=[O:17])=[O:16])[CH:11]=[CH:10][C:9]=1[N+:21]([O-])=O)(=[O:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+]>[Fe].O>[OH:1][CH2:2][CH2:3][S:4]([CH2:7][C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH2:18][CH2:19][OH:20])(=[O:17])=[O:16])[CH:11]=[CH:10][C:9]=1[NH2:21])(=[O:6])=[O:5]

Participants

Procedure

100 parts of 2,4-bis(hydroxyethylsulfonylmethyl)nitrobenzene are added at a constant rate over a period of 30 minutes with stirring to a mixture heated to 80° to 85° C. and consisting of 40 parts of iron powder and 200 parts of water, the reaction temperature being maintained at 80° to 85° C. during the addition. After the addition is completed, stirring is continued for 30 minutes, the pH is adjusted to 8.5 with aqueous sodium carbonate solution, and the mixture is clarified while hot by removing the precipitated iron hydroxide. The filter residue is washed twice with a small amount of hot water. The combined filtrates are subsequently concentrated in vacuo to 150 parts by volume and subsequently cooled to 0° to 5° C. with stirring. The slightly brownish precipitate is isolated on a nutsche filter, covered with a small amount of ice water and dried in vacuo at 60° C. This gives 84.7 parts of 2,4-bis(hydroxyethylsulfonylmethyl)aniline of the formula ##STR23## of melting point 183° to 185° C. and a purity (by diazotization) of 99.5%.