Monatshefte fuer Chemie published new progress about 14807-75-1. 14807-75-1 belongs to ethers-buliding-blocks, auxiliary class Salt,Thiourea,Amine,Aliphatic hydrocarbon chain, name is Formamidine disulfide dihydrochloride, and the molecular formula is C22H18O2, Formula: C2H8Cl2N4S2.
Ziegler, E. published the artcileSyntheses of heterocyclics. XLI. Cyclic dichloromalonyl compounds, Formula: C2H8Cl2N4S2, the publication is Monatshefte fuer Chemie (1962), 1376-82, database is CAplus.
cf. ibid. 1062-4; CA 57, 9850b. The method of Baeyer and Bloem (Ber. Deut. Chem. Ges. 15, 2150 (1882)) for chlorination of 4-hydroxycarbostyril (I) was examined in various solvents. Thus, 60 g. I was heated to boiling in a mixture of 220 ml. dioxane, 100 ml. concentrated HCl, and 40 ml. H2O. After heating was stopped, 200 ml. 30% H2O2 was quickly added. After 15 min. the oil which separated gradually crystallized to give 91% 3,3-dichloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline (II), m. 175° (C6H6). Yields in other solvents were: H2O-AcOH, 70%; EtOH, 58%. The following substituted 2,4-dioxo-1,2,3,4-tetrahydroquinolines were prepared in the same way (yield, m.p.): 3,3-dichloro-6,8-dimethyl, quant., 215° (C6H6); 1-methyl-3-benzyl-3-chloro (III), 97%, 136.0-6.5° (MeOH). 5,5-Dichlorobarbituric acid, m. 211-15° (dilute HCl), was prepared similarly in 80% yield from barbituric acid, while 5 g. 1-phenyl-3-methyl-2-pyrazolin-5-one was converted in 96% yield to its 4,4-dichloro derivative (IV), m. 61° (dilute alc.). A suspension of 40 g. I in 100 ml. dioxane was heated to 50°, stirred, and 55 ml. SO2Cl2 added slowly. Solution began and the mixture was boiled for a short time, cooled, and treated with 300 ml. ice-H2O to give 96% II. The following 2,4-dioxo-1,2,3,4-tetrahydroquinoline derivatives were prepared from the corresponding 4-hydroxycarbostyrils (yield, m.p.): 3,3-dichloro-6-fluoro, quant., 119° (EtOH); 3,3-dichloro-1-phenyl (V), quant., 200° (PhCl); 3,3-dichloro-1-benzyl (VI), quant., 122° (EtOH); 3-benzyl-3-chloro, 96%, 186° (AcOH). 5-Chlorobarbituric acid, m. 280-90° (decomposition) (H2O), was similarly prepared in 79% yield. I (4 g.) in 25 ml. dioxane and 15 ml. H2O was treated with Cl at 80° for 10-15 min., cooled, and 30 ml. H2O added to give 96% 3,3,6-trichloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline, m. 230-2° (EtOH). II (3 g.) was dissolved in 30 ml. EtOH and 10 ml. AcOH by boiling and 3 g. Zn dust added in small portions. Decolorization began in a few min., after which 150 ml. H2O was added to precipitate 96.5% 3-chloro-4-hydroxycarbostyril (VII), which sintered at 270° and m. 275-80° (decomposition) (EtOH). Also prepared (name, starting compound, yield, m.p.) were: 1-phenyl-3-methyl-4-chloro-2-pyrazolin-5-one, IV, 94%, 153°; 1-phenyl-3-chloro-4-hydroxycarbostyril, V, quant., 264° (EtOH); 1-benzyl-3-chloro-4-hydroxycarbostyril, VI, quant., 253-4° (BuOH); 1-methyl-3-benzyl-4-hydroxycarbostyril, III, 86%, 213°. VII also was prepared in 94% yield by treating 0.2 g. II with 10 ml. 5% I in dioxane and 0.5 ml. concentrated HCl. CS(NH2)2 (3 g.) was partly dissolved in 40 ml. absolute EtOH and 1 ml. alc. HCl by heating at 50°, then the solution of II was added in small portions. Cooling caused precipitation of 2.5 g. diamidino disulfide dihydrochloride, m. 170° (decomposition).
Monatshefte fuer Chemie published new progress about 14807-75-1. 14807-75-1 belongs to ethers-buliding-blocks, auxiliary class Salt,Thiourea,Amine,Aliphatic hydrocarbon chain, name is Formamidine disulfide dihydrochloride, and the molecular formula is C22H18O2, Formula: C2H8Cl2N4S2.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem