Manufacture and Production of Ureas or Thioureas of the Naphthalene Series

20,192. Newton, P. A., [Farbenfabriken vorm. F. Bayer & Co.]. Sept. 25. Samples furnished. Ureas and thioureas of the naphthalene series are obtained by the following processes: (1) condensing nitroarylolefincarboxylic acid chlorides, nitroarylfatty acid chlorides, nitronaphthoyl chlorides, nitronaphthalene sulphochlorides, or substitution products thereof, with 1 :8-aminonaphthol sulphonic acids or substitution products thereof, reducing the nitro group in the compounds so obtained, and converting the resulting amino compounds into ureas by treatment with phosgene or the like; (2) condensing aromatic nitroacidyl halides, such as nitrobenzoyl chlorides, nitrobenzene sulphochlorides, nitroarylolefincarboxylic acid chlorides, nitroarylfatty acid chlorides, nitronaphthoyl chlorides, nitronaphthalene sulphochlorides, or substitution products thereof, with naphthylamine sulphonic acids, or aminonaphthol sulphonic acids (other than 1.:8-aminonaphthol sulphonic acids) or substitution products thereof, reducing, and treating with phosgene, &c., as above; (3) condensing nitroacidyl halides, such as those specified above, with naphthylamine sulphonic acids or aminonaphthol sulphonic acids, or substitution products thereof, reducing the nitro group in the products obtained, and converting the amino compounds into thioureas by treatment with thiophosgene or the like. In the processes described above, the amino compounds formed may be again condensed with nitroacidyl halides. and the products reduced to amino compounds, this process being repeated further if desired, and the amino compounds are finally converted into ureas or thioureas. The products have therapeutic properties in the treatment of diseases due to blood parasites, or may be used in the production of substantive dyes. According to examples, ureas are prepared from maminobenzoyl-m-aminobenzoyl-1-aminonaphthalene-3: 6-disulphonic acid and m-amino-pmethoxybenzoyl-1-aminonaphthalene-5-carbonyl- 1-amino-8-naphthol-4:6-disulphonic acid. The following parent materials also are specified: p-nitrobenzoyl chloride, o-chlor-p-nitrobenzoyl chloride, m-nitrocinnamyl chloride, p-nitrophenylacetyl chloride, 1-nitronaphthalene-5- sulphochloride; 1-amino-7-brom-8-naphthol-3:6- disulphonic acid, 1:4:6-, 2:3:6-, or 2:4:8- naphthylamine disulphonic acids, 1:4:6:8- naphthylamine trisulphonic acid, chlornaphthylamine sulphonic acids, for example, 8-chlor- 1-naphthylamine-3:6-disulphonic acid, alkyloxynaphthylamine sulphonic ac