Patent GB-655435-A (GB)
Title: Organo arsenic and antimony compounds
IPC: C07F9/92
Filed: 1948-01-26
Abstract: Organo arsenic and antimony compounds of the formula <FORM:0655435/IV (b)/1> wherein R1 is a phenyl radical, Me is a trivalent atom of arsenic or antimony and R2 has the significance indicated below, are prepared by reacting in a liquid reaction medium a compound of the formula R1-MeX, wherein R1 has the above significance and X represents =O, =S, two halogen atoms such as chlorine, bromine or iodine, or two residues of organic monomercapto compounds, with a dimercapto compound of the formula (HS)2R2, wherein R2 is aliphatic or aromatic containing at least three carbon atoms and in which the -SH groups are attached to vicinal carbon atoms.  A suitable reaction medium is any organic solvent or a mixture of solvents, e.g. propylene glycol, preferably in anhydrous condition.  One mol. of the compound R1-MeX may be reacted with at least one mol. of the dimercapto compound.  The reactant R1-MeX may be a compound of the type R1-Me=(SR1)2, wherein SR1 is the residue of an organic monomercapto compound of the formula HSR1.  An organometallic compound of pentavalent arsenic or antimony may be reduced to give the R1-MeX compound, e.g. as described in Specification 592,875, which is then reacted in situ with the dimercapto compound.  The reaction may be carried out with the aid of an organic monomercapto or dimercapto compound.  Compounds mentioned having -SH groups attached to vicinal carbon atoms are 2,3-dimercaptopropanol, 1,2-propanedithiol, 1,2 - ethanedithiol, 2,3 - dimercaptopropanol, 1,2 - propanedithiol, 1,2 - ethanedithiol, 2,3 - butanedithiol, 1,3 - dithioglycerol, 1,2- and 1,3 - dimercaptobenzene, dithio - o - xylene glycol, C6H4(CH2SH)2, dithiopenterythritol, 2,3-dimercaptopropyl ethyl ether and 2,3 - dimercaptopropanol - glucoside.  The reduction of the organo pentavalent arsenic or antimony compound to give the R1-MeX compound may be effected with thiolactates, thioglycolates, thiomalates or other similar thioacids.  When the group R1 in the desired product is a phenyl radical containing an amino group, e.g. in the para position to the arsenic or antimony atom, the product may be acetylated or reacted with 2,4-diamino-6-chloro-1,3,5-triazine to introduce a triazine substituent on the amono group.  The triazine substituent may be present, however, in the R1-MeX reactant before reaction with the dimercapto compound.  A large number of detailed examples are given where the group R1 has various substituents. Specifications 573,933, and 587,015 also are referred to.  The Specification as open to inspection under Sect. 91 refers to the above process wherein the group R1 in the desired product is any cyclic organic radical.  This subject-matter does not appear in the Specification as accepted.ALSO:An internal remedy is obtained by dissolving in an organic solvent or a mixture of solvents an organo arsenic or antimony compound of the formula <FORM:0655435/VI/1> wherein R1 is phenyl radical which may have substituents, Me is a trivalent atom of arsenic or antimony and R2 is an aliphatic or aromatic radical having at least three carbon atoms and having the sulphur atoms attached to vicinal carbon atoms. The solvent may be propylene glycol, preferably in anhydrous condition.  The internal remedy may contain 2, 3-dimercaptopropanol, thioglycollic acid or cystein.  Ascorbic acid may also be added.  The Specification as open to inspection under Sect. 91, the group R1 in the above formula may represent any cyclic organic radical.  This subject-matter does not appear in the Specification as accepted.