Patent GB-447773-A (GB)
Title: Manufacture of arsenobenzene-monosulphoxylates
IPC: C07F9/74
Filed: 1934-11-24
Abstract: Arsenobenzene compounds of the general formula <FORM:0447773/IV/1> in which R and R<1> represent hydroxyalkyl groups, are prepared by (1) reducing a bis-hydroxyalkylamino - hydroxybenzene - arsonic acid together with an aminohydroxybenzenearsonic acid and treating the product with sodium formaldehyde-sulphoxylate; or (2) reacting upon an aminohydroxyarsenobenzene-monosulphoxylate with two molecular proportions of alkylene oxide.  The products possess therapeutic properties.  According to the examples: (1) a mixture of 3-(bis-dihydroxypropyl) - amino - 4 - hydroxybenzene - 1 - arsonic acid and 3-amino-4-hydroxybenzene-1-arsonic acid is reduced with hypophosphorous acid or sodium hydrosulphite and the product treated with sodium formaldehyde-sulphoxylate; 4-(bis - dihydroxypropyl) - amino - 3 - hydroxy-benzene-1-arsonic acid may replace the first starting material in the same process; (2) 3 : 3<1>-diamino-4 : 4<1>-dihydroxy-arsenobenzene-monosulphoxylate is heated with glycide to give the corresponding 3-(bis-dihydroxypropyl)-amino-3<1>-amino compound; (3) 3-hydroxy-4-(bis-dihydroxyethyl) - amino - 3<1> - hydroxy - 4<1>-aminoarsenobenzene-monosulphoxylate is obtained by treating the corresponding 4-amino compound with ethylene oxide. Specification 226,686, [Class 2 (iii)], is referred to.  The samples furnished under Sect. 2 (5) comprise 3 - (dihydroxypropyl - hydroxyethyl) -amino-4-hydroxy-3<1>-amino-4<1>-hydroxyarsenobenzene - monosulphoxylate prepared by (1) treating 3 : 3<1>-diamino-4 : 4<1>-dihydroxyarsenobenzene-monosulphoxylate first with glycide and then with ethylene oxide, or (2) reacting on 3 - amino - 4 - hydroxybenzene - 1 - arsonic acid successively with ethylene oxide and glycide, reducing the product together with 3-amino-4-hydroxybenzene-1-arsonic acid and finally treating with sodium formaldehyde-sulphoxylate.  Arsonic acids.--3 - (Bis - dihydroxypropyl)-amino - 4 - hydroxybenzene - 1 - arsonic acid and 3 - hydroxy - 4 - (bis - dihydroxypropyl) - amino-benzene-1-arsonic acid are prepared by treating the corresponding amino compound with excess of glycide.  The Specification as open to inspection under Sect. 91 is not restricted to the preparation of of arsenobenzene compounds containing a hydroxyl group in each nucleus, and describes the preparation of (1) 3-(bis-hydroxyethyl) -amino-4-hydroxy-3<1>-amino-4<1>-hydroxyarsenobenzene - monosulphoxylate by reducing a mixture of 3 - (bis - hydroxyethyl) - amino - 4-hydroxybenzene-1-arsonic acid, obtained by treating the amino compound with ethylene oxide, and 3-amino-4-hydroxybenzene-1-arsonic acid with hypophosphorous acid, and treating the product with sodium formaldehyde - sulphoxylate; (2) 4-(dihydroxypropyl-hydroxyethyl) -amino-3<1>-amino-4<1>-hydroxyarsenobenzene -monosulphoxylate by reducing with hypophosphorous acid a mixture of 3-amino-4-hydroxybenzene - 1 - arsonic acid and 4 - (dihydroxypropyl-hydroxyethyl)-aminobenzene-1-arsonic acid, obtained by reacting upon arsanilic acid first with ethylene oxide and then with glycide, and treating the product with sodium formaldehyde - sulphoxylate.  This subject-matter does not appear in the Specification as accepted.