Patent GB-531590-A (GB)
Title: Process for the manufacture of phosphoric acid dichlorides of substituted sulphanilic acid anilides
Filed: 1939-07-27
Abstract: 531,590. Phosphoric acid dichlorides of substituted sulphanilic acid anilides. HOFFMANN-LA ROCHE & CO., AKT.-GES., F. July 27, 1939, No. 21832. Convention date, July 30, 1938. Addition to 527,548. [Class 2 (iii)] The process of the parent Specification in which amino-benzene-sulphonamides are heated with phosphorus oxychloride to give phosphoric acid dichlorides of the formula Cl 2  ,PONR-C 6 H  5 -SO  2 NR<SP>1</SP>R<SP>11</SP> where R is alkyl or hydrogen, R<SP>1</SP> is alkyl, aryl, or hydrogen and R<SP>11</SP> is alkyl or hydrogen is modified in that there are used as starting materials substituted sulphanilic acid anilides, which can be used as such or in the form of their salts. Starting materials mentioned include 4-amino-benzene sulphonyl sulphanilamide, 4- amino-benzene sulphonyl silphanilic acid dimethyl amide, sulphanilic acid -4-nitro anilide, sulphanilic acid-4-amino anilide, sulphanilic acid-3-amino anilide. In examples (1) 4-aminobenzene sulphonyl sulphanilic acid dimethyl amide is boiled with phosphorus oxychloride, and the solution poured in a mixture of equal parts of benzene and petroleum ether. The phosphoric acid dichloride which separates has the formula Cl 2 PONHÀC 6 H 4 ÀSO 2 ÀNHÀC 6 H 4 ÀSO 2 N(CH 3 ) 2  (2) Phosphorus oxychloride and sulphanilic acid- 4-amino anilide are reacted as in example (1) to give Cl 2 PONHÀC 6 H 4 SO  2 NHÀC 6 H  4 NHÀPOCl 2  (3) Phosphorus oxychloride and sulphomilic acid - 4-nitro anilide are reacted as in example (1) to give Cl 2 PONHÀC 6 H 4 ÀSO 2 ÀNHÀC 6 H 4 NO 2  The Specification as open to inspection under Sect. 91 includes also the general reaction of phosphorus oxychloride with any bactericidal compounds containing sulphur and possessing one or several amino groups. As starting materials for reaction with the phosphorus oxychloride there are included also sulphurous compounds having a bactericidal action without sulphonamide groups such as derivatives of diaryl sulphides, diaryl disulphides and the corresponding sulphoxides and sulphones, for instance 4:4<SP>1</SP>-diamino-diphenyl sulphide, 4:4<SP>1</SP>- diamino diphenyl sulphoxide, 4:4<SP>1</SP>-diamino diphenyl sulphone, 4-amino-41-nitro-diphenyl sulphone ; also bactericidal derivatives of diaryl sulphide (sulphoxide, sulphone) sulphonamides, such as for instance 4-amino-diphenyl sulphide 4<SP>1</SP>-sulphonamide, 4-aminodiphenyl sulphone-4<SP>1</SP>-sulphonamide ; bactericidal derivatives of arylalkyl sulphides sulphoxide and sulphones such as 4-amino-thiophenol propyl ether. The following additional examples were also present (1) 4:4<SP>1</SP>-diamino-diphenyl sulphide is boiled with phosphorus oxychloride, and the reaction product poured into a mixture of equal parts of benzene and petroleum ether when the reaction product solidifies. It is a compound of the formula Cl 2 PONHÀC 6 H  4 ÀSÀC 6 H  4 ÀNHÀPOCl 2  (2) Phosphorus oxychloride and 4:4<SP>1</SP>-diaminodiphenyl-sulphoxide are reacted and worked up as in the previous example to give a product of the formula Cl 2 PONHÀC 6 H 4 ÀSOÀC 6 H 4 NHPOCl 2  This subject-matter does not appear in the Specification as accepted.