Patent GB-534150-A (GB)
Title: Process for the manufacture of phosphoric acid derivatives of derivatives of sulphanilic acid
Filed: 1939-08-22
Abstract: 534,150. Phosphoric acid derivatives of sulphonilic acid. HOFFMAN-LA ROCHE & CO. AKT.-GES., F. Aug. 22, 1939, No. 24152. Convention date, Aug. 27, 1938. [Class 2 (iii)] The phosphoric acid dichlorides of 4-aminobenzene-sulphonamides and of substituted sulphonilic acid anilides which are prepared by the processes of Specifications 527,548 and 531,590 are reacted with sulphanilic acid amides and substituted sulphanilic acid anilides to give phosphoric acid chlorides which on decomposition with water or aqueous bases form phosphoric acids having a bactericidal action and which form neutral salts soluble in water. The amides and anilides may also be heated with the phosphoric acid dichlorides after the addition of tertiary bases such as dimethylaniline or in the form of their salts. Phosphoric acid derivatives can be prepared containing two bactericidal components which may be either identical or different. In examples (1) Phosphoric acid dichloride-4- sulphonamidoanilide and sulphanilamide are mixed and heated with the exclusion of water. The reaction product is treated with excess of caustic soda and then with acid to give a phosphoric acid-di-4-sulphonamidoanilide of the formula PO(OH) (NHC 6 H 4 JO 2 NH 2 ) 2  ; (2) Phosphoric acid dichloride-4-sulphonamidoanilide and sulphanilamide hydrochloride are reacted as in example (1) to give the same products ; (3) The same starting materials as in example (1) are heated and worked up by the same method except that phosphoric acid is used to acidify the reaction products ; (4) As in example (1) except that the solid reaction product is dissolved in water before being treated with caustic soda; (5) The reaction components of example (1) are heated after the addition of dimethylanilines, which is removed after the reaction to give the product of example (1) ; (6) p-Amino-benzenesulphonylsulphanilic acid-dimethylamide is heated with phosphorus oxychloride and the resulting phosphoric acid dichloride is treated with sulphanilamide in the absence of water, and the product worked up as before to give a compound of the formula NH 2 O 2 SC 6 H 4 NHPO(OH)NH C 6 H 4 SO 2 NH C 6 H 4 SO 2 N(CH 3 ) 2  ; (7) The phosphoric acid dichloride obtained by heating sulphanilic acid-4-nitroanilide with phosphorus oxychloride is heated with sulphanilamide to give a product of the formula NH 2  02 S.C 6 H 4  The compound is purified by the addition of small amounts of acetic acid ; (8) The phosphoric acid dichloride obtained by heating sulphanilic acid-4-aminoanilide with phosphorus oxychloride is heated with sulphanilamide to give a product of the formula NH 2  O 2  S.C 6  H 4  The Specification as open to inspection under Sect. 91 includes also the reaction of any phosphorus dichlorides of bactericidal compounds containing sulphur which are described in Specifications 527,548 and 531,590 as open to inspection under Sect. 91, with sulphurous bactericidal amino compounds. This expression includes compounds which have no sulphonamide group. An additional example is, also included as follows :-The phosphoric acid dichloride obtained by heating sulphanilic acid - 4 - aminoanilide with phosphorus oxychloride is heated with sulphanilamide in the absence of moisture. The solid reaction product is worked up as. before to give a compound of the formula NH 2 O 2  S.C 6 H 4  NH PO (OH) NHC 6  H 4  SO 2  NHC 6  H 4  NH PO (OH) NH C 6  H 4  SO 2  NH 2 . This subjectmatter does not appear in the Specification as accepted.