water. tively into carbonyldichlorophenol. It is very slowly decomposed by The B-compound forms white needles melting at about 89°. Cold alcohol decomposes it with evolution of chlorine. Both compounds explode when quickly heated. Carbonyltrichlorophenolch lorimide, C,HCI,NO,, crystallises in white needles, which begin to decompose above 130°, and detonate when heated quickly. Boiling water and boiling alcohol convert it quantitatively into carbonyltrichlorophenol. Carbonyltetrachloramidophenol, CHCI,NO2, is obtained by carefully exploding small amounts of the chlorimide in a capacious flask. It melts at 220-237°, is soluble in alcohol, ether, and benzene, less soluble in water; it could not be obtained quite pure. Bleaching powder precipitates carbonyltetrachlorophenolchiorimide from the solu tion in glacial acetic acid. Carbonylbromamidophenol (m. p. 186-187°) when treated with chlorine water, yields a chlorimide, C,H,C1BrNO2, which melts at 118-120° and resembles the other chlorimides. Carbonyldibromamidophenol, C,H,Br2NO2, obtained by the action of an excess of bromine-water on carbonylamidophenol, crystallises from alcohol in plates which melt at 243-245° with partial decomposition. It is insoluble in cold water. The silver salt forms white needles. The chlorimide, C,H,Br2CINO2, crystallises in large needles melting at 120°. N. H. M. Secondary Diamines containing an Ethylene-group. By A. COLSON (Bull. Soc. Chim., 48, 799-802; compare this vol., p. 139).Ethylene orthoditolyldiamine, C2H.(C,H,N)2, is prepared by heating a mixture of orthotoluidine and ethylene bromide. It is crystalline, dissolves in ether (7 parts), cold alcohol (10 to 12 parts), and boiling water (300 parts). The alcoholic solution (not the aqueous) reacts with acidified methyl-orange. The hydrobromide forms white crystals soluble in 30 parts of boiling water; the hydrochloride is sparingly soluble. N. H. M. Action of Nitrous Acid on some Organic Bases. Dinitrosobenzenylamidine. By W. LOSSEN and F. MIERAU (Ber., 21, 12501256).-Benzenylamidine nitrite, NH, CPh-NH,HNO, + H2O, is obtained by evaporating a neutral solution of benzenylamidine hydrochloride with sodium nitrite. It forms well-defined plates which lose their water of crystallisation, and are gradually decomposed at 64°; heated at a higher temperature, it yields benzonitrile, nitrogen, and water. It is readily soluble in water and alcohol, but insoluble in ether; it shows all the properties of a nitrite. Dinitrosobenzenylamidinebenzenylamidine, CH,N,O2, is formed by the action of nitrous acid on benzenylamidine in an acid solution. It crystallises in leaves which are sparingly soluble in cold water or alcohol, more readily in hot water, very readily in hot alcohol, but almost insoluble in ether. It explodes when heated at 178°, and is decomposed by an excess of acid with evolution of gas. Potassium dinitrosobenzenylamidine, C,H,KN(NO)2, is obtained by adding potash to a hot alcoholic solution of the preceding compound. It crystallises in needles which are readily soluble in water, sparingly in alcohol, and insoluble in ether. In the dry state, the salt is very explosive, but in aqueous solution can be boiled without any decomposition taking place. An aqueous solution gives precipitates with barium chloride, lead acetate, and mercurous nitrate; ammonia, hydroxylamine hydrochloride, and methylaniline hydrochloride throw down precipitates of slender, colourless needles. The metallic precipitates. are explosive in the dry state. An aqueous magenta solution produces a voluminous, dark-red precipitate. Silver dinitrosobenzenylamidine, C,H,Ag(NO)2N2, is also very explo sive. F. S. K. Mixed Diazo-compounds. By H. GOLDSCHMIDT and J. HOLM (Ber., 21, 1016-1026).-Diazobenzenebenzylamine, PhN, NH·CH2Ph, is formed by the action of diazobenzene chloride on benzylamine; it crystallises from hot light petroleum in pale-yellow, thin, transparent leaves, melting at 72°, and is readily soluble in ether, benzene, and alcohol. This compound, like its higher homologues, is very readily acted on by acids; when boiled with hydrochloric acid, it behaves like a mixture of diazobenzenebenzylamine and diazobenzylaniline. Paradiazotoluenebenzylamine, C,H,Me N2 NH·CH,Ph, is obtained by the action of paradiazotoluene chloride on benzylamine; it forms slightly yellowish leaves melting at 77°, and is readily soluble in benzene, alcohol, and ether. When boiled with hydrochloric acid, it reacts like a mixture of diazobenzyltoluidine with a smaller quantity of diazotoluenebenzylamine. Orthodiazotoluenebenzylamine is obtained in the form of a darkyellow oil by the action of orthodiazotoluene chloride on benzylamine. B-Diazonaphthalenebenzylamine, CH, N2 NH-CH,Ph, is produced by the action of B-diazonaphthalene chloride on benzylamine; it separates from ether and benzene in brownish crystals melting at 110°. New Method for Determining the Constitution of Mixed Diazoamidocompounds.When the reaction product of diazobenzene chloride and benzylamine is dissolved in benzene, warmed for a few minutes with 1 mol. of phenyl isocyanate, and the benzene evaporated in a vacuum, a product is obtained which crystallises from alcohol in long, slender, snow-white needles melting at 119°. Analysis showed that this compound consists of 1 mol. of phenyl isocyanate in combination with 1 mol. of the diazoamido-compound. Two formulæ are possible for this substance, NHPh-CO-N(CH2Ph)N,Ph and NHPh CONPh•N,CH,Ph. When boiled with hydrochloric acid, it yields benzylphenylcarbamide, phenol, and a small quantity of benzyl chloride, which shows that the first formula is the correct one. The diazoamido-compound is therefore diazobenzenebenzylamine. Similarly, the condensation-product of paradiazotoluene chloride and benzylamine yields with phenyl isocyanate a compound C21H20N,O, which crystallises from alcohol in slender, white needles melting at 115-116°. By boiling this substance with hydrochloric acid, benzyl VOL. LIV. 2% phenylcarbamide, paracresol, and a small quantity of benzyl chloride are obtained, showing that the diazoamido-compound is paradiazotoluenebenzylamine. From these experiments, it follows that the reaction between diazochlorides and benzylamine is normal. Dis-paradiazotoluene-ethylamine, NEt(N, C,H,Me),, is formed by the action of paradiazotoluene chloride on ethylamine. It crystallises from ether in bright-yellow, transparent needles which melt at 121° with copious evolution of gas; it is readily soluble in ether, benzene, and hot light petroleum, sparingly in ether and cold light petroleum. When boiled with dilute sulphuric acid, it yields paratoluidine, paracresol, ethylamine, ethyl alcohol, and nitrogen. F. S. K. Substitution-products of Parazotoluene. By J. V. JANOVSKY and K. REIMANN (Ber., 21, 1213-1219; compare Abstr., 1887, 479).— Three substitution-products are obtained by the action of bromine on parazotoluene in glacial acetic acid solution. 4 2 1 2 4 Orthobromazotoluene, CH,MeBr N2 C,H,Me, separates from the glacial acetic acid solution and, after recrystallising from alcohol, is obtained in golden-orange-coloured, rhombic plates melting at 139°. 4 2 1 4 3 Bromazotoluenesulphonic acid, C,H,MeBr·N2•CH,Me·SO2H + 14H2O, is formed by acting on the preceding compound with sulphuric acid containing sulphuric anhydride. It yields very characteristic salts which are mostly sparingly soluble in water. The potassium salt, C1H12BrN2SO,K, crystallises in rhombic prisms. The sodium salt forms large, anhydrous, shining, golden prisms. The copper and cadmium salts are yellow, crystalline compounds. Paratoluidineorthosulphonic acid and metabromoparatoluidine are obtained when the acid is treated with tin and hydrochloric acid. Metabromazotoluene remains in the mother-liquor from the orthocompound, and is precipitated on adding water. It crystallises from alcohol in small, orange-yellow leaflets which are readily soluble in ether, acetone, and benzene, and melt at 128°. When treated with alcoholic ammonia and hydrogen sulphide, a hydrazobromotoluene, melting at 113°, is obtained. It yields a sulphonic acid, the sodium, potassium, and copper salts of which are readily soluble, and the acid, when reduced with tin and hydrochloric acid, gives paratoluidinemetasulphonic acid [Me: SO,H: NH, 1:3: 4] and orthobromoparatoluidine [Me: Br: NH2 = 1: 2: 4], melting at 20-23°. = The bromazotoluenesulphonic acid previously described (loc. cit.) must have the constitution [Me : Br: N2: SO,H: Me = 4:3:1:3: 4]. Dimetadibromazotoluene, N2(C&H3BrMe), [Me: Br: N = 1:2:4], is contained in the mother-liquor from the metabromazotoluene. It is a yellow, crystalline compound melting at 75°. When reduced, it yields orthobromtoluidine melting at 25°. F. S. K. Action of Carbonyl Chloride on Hydrazides. By M. FREUND and B. B. GOLDSMITH (Ber., 21. 1240-1244). Malonyl hydrazide, CH2(CO·NH NHPh)2, obtained by heating ethyl malonate or malonamide with phenylhydrazine, crystallises from dilute alcohol in white leaflets which melt at 187°, are insoluble in water, but dissolve readily in alcohol, chloroform, and glacial acetic acid. When heated with a benzene solution of carbonyl chloride, a compound, CH12N,O1, is obtained which crystallises from glacial acetic acid in yellowishcoloured leaves melting at 205°; it is very sparingly soluble in water and alcohol, and only sparingly soluble in benzene. Ethylmalonyl hydrazide, CHEt(CO·NH NHPh), prepared by heating ethylmalonamide with phenylhydrazine, crystallises from glacial acetic acid in white needles which melt at 233°; it is sparingly soluble in alcohol and insoluble in water. When treated with carbonyl chloride, it yields a compound, C9H16N,O, which crystallises from glacial acetic acid or alcohol, and melts at 112-113°. Oxalyl hydrazide and carbonyl chloride give a product, CH10N,O, which is not acted on by alkalis or concentrated hydrochloric acid, and crystallises in microscopic forms melting above 300°. Acetyl hydrazide and carbonyl chloride yield a compound, C16H16N4O4, which crystallises from dilute alcohol in white prisms. It melts at 93-94°, and can be distilled without decomposition. F. S. K. Action of Carbamide on Hydrazines. By A. PINNER (Ber., 21, 1219-1227; compare Abstr., 1887, 1042; also Skinner and Ruhemann, this vol., p. 274).-Phenylurazole is formed by heating phenylsemicarbazide with carbamide (2 mols.) at 150-160°; also by heating a mixture of phenylhydrazine hydrochloride and biuret suspended in amyl alcohol. Orthotolylsemicarbazide, CHNO, is produced when orthotolylhydrazine is heated with carbamide (2 mols.). It crystallises in flat, compact needles melting at 159-160°, is tolerably readily soluble in water, sparingly in alcohol, and insoluble in ether and benzene. It reduces Fehling's and ammoniacal silver solution. Orthotolylurazole, C,H,NO2, is obtained by heating tolylhydrazine hydrochloride with carbamide (4 mols.). It forms white leaflets. which melt at 170° and dissolve readily in hot, tolerably readily in cold water. It dissolves in dilute alkalis and ammonia, forming reddish solutions. Paratolylsemicarbazide crystallises in shining leaves melting at 157-158°. It is only sparingly soluble in cold water, but dissolves rather easily in alcohol and hot water. It reduces ammoniacal silver and alkaline copper solutions. Paratolylurazole crystallises in slender, yellowish needles which melt at 274° with decomposition. It is very sparingly soluble in both hot and cold water. a-Naphthylsemicarbazide, CH,NH-NH·CONH2, is formed when a-naphthylhydrazine hydrochloride and carbamide are heated together at 140°. It crystallises from boiling amyl alcohol in thin, shining, slightly brownish leaves which melt at 231° and are insoluble in water and ether. It is sparingly soluble in alcohol, benzene, ammonia, and dilute alkalis, and reduces Fehling's solution. B-Naphthylsemicarbazide forms thin leaves which melt at 225° and towards solvents behaves like the a-compound. Nitrous acid has no action on phenylurazole; bromine and phosphorous pentachloride react only at a high temperature causing complete decomposition. Dimethylphenylurazole, CH,MeN3O2, was obtained in an impure state by heating the urazole with potash, methyl iodide, and a small quantity of methyl alcohol. It crystallises in white needles melting at 90°. The acetyl-derivative, CH,Ac2NO2, crystallises from benzene in white needles which melt at 141-149°, and are insoluble in water. When phenylsemicarbazide is heated at 160-170° for four to five hours, ammonia, carbonic anhydride, carbon monoxide, and benzene are evolved and a brownish, vitreous mass remains. This residue consists chiefly of unchanged semicarbazide mixed with a considerable quantity of phenylurazole, but it also contains a new compound which remains behind in the form of a white, crystalline, granular mass when the residue is extracted with boiling water. This compound has the empirical formula C,H,N2O; it melts at almost the same temperature as phenylurazole (264°) and, like the latter, dissolves readily in alkalis and ammonia; it is, however, very sparingly soluble in hot water, hot alcohol, and other solvents. It dissolves in ammonia without change, but when precipitated from its solution in soda it melts at 231°. F. S. K. Phenosafranine. By P. BARBIER and L. VIGNON (Bull. Soc. Chim., 48, 338-342).-When a mixture of paraphenylenediamine and aniline (eq. mols.) is oxidised at a low temperature, a blue compound is obtained which changes gradually at the ordinary temperatures, instantly at 100°, into phenosafranine. Owing to its instability, the blue compound could not be analysed, but its conversion into phenosafranine is shown to take place without addition or elimination of any substance. It is converted by the action of zinc and hydrochloric acid at a low temperature into aniline and a new leuco-base which, when exposed to air, yields amidophenazine, C ̧H ̧ |уCH, NH2, the hydrochloride of which crystallises in slender, violet-red needles. When this is reduced with zinc and hydrochloric acid, the leuco-base, C2H<H>C2H2•NH2, is obtained. By oxidising this leuco-base in presence of aniline at a low temperature, the blue compound is regenerated. NH 3 The constitutional formulæ, N ̧C6H3(NH2), N C&H ‚C2H3(NH2). NCI NHPh, are ascribed to safranine and to the blue compound respectively. N. H. M. Alkylformanilides. By A. PICTET and P. CRÉPIEUX (Ber., 21, 1106-1111).-Alkylformanilides can readily be prepared by dissolv |