Bis(hydroxyethylsulfonylmethyl)anilines and a process for their

Details Bis(hydroxyethylsulfonylmethyl)anilines and a process for their Bis(hydroxyethylsulfonylmethyl)anilines and a process for their

1988-09-29

1990-10-02

Reamer, James H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

568 30, 568 32, 568 46, C07C31726

Patent

active

049609408

ABSTRACT:
A process for the preparation of compounds of the formula ##STR1## in which the side chains --CH.sub.2 --SO.sub.2 --CH.sub.2 --CH.sub.2 --OH are in the ortho-, meta- or para-position relative to one another and the amino group is in the 4-position in the case where the two side chains are in the 1,2- or 1,3-position, by reacting 1 mol of xylylene dichloride with at least 2 mol of mercaptoethanol at 40.degree.-150.degree. C. in an aqueous medium in the presence of an acid-binding agent to give the corresponding compound of the formula ##STR2## oxidizing this product with at least 4 mol of hydrogen peroxide at 50.degree.-120.degree. C. at a pH<7 in the presence of tungsten(VI) compounds to a compound of the formula ##STR3## converting this product with anhydrous sulfuric acid at 30.degree.-45.degree. C. to the corresponding bis(sulfuric ester), nitrating the latter with high-percentage nitric acid at 0.degree.-60.degree. C. to give the bis(sulfatoethylsulfonylmethyl)nitrobenzene, hydrolyzing this product after the addition of water by heating followed by reduction.

REFERENCES:
patent: 3201434 (1965-08-01), Tesoro
patent: 3394154 (1968-07-01), Braus et al.
patent: 3449439 (1969-06-01), Kuhnen et al.
patent: 4612394 (1986-09-01), Katero et al.

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