Imines, hydrochloride

Auramine O (4,4 -bis-dimethylaminobenzophenone imine hydrochloride) [2465-27-2] M 321.9, pK 10,71 (free base), 9.78 (carbinolamine). Crystd from EtOH as hydrochloride, very slightly soluble in CHCI3, UV 434 (370) nm. The free base has m 136 after crystn from benzene. [J Chem Soc 1724 1949 Biochemistry 9 1540 1970]. 

The related sydnone imine hydrochloride 147 has also been isolated in low yield by treating N-nitroso-A -diphenylphosphinylmethylglycinonitrile 146 with anhydrous HQ and ether at low temperature (2), in a manner similar to that described previously for other nitrosamines of aminoacetonitrile (80). 

N-Nitroso-sydnon-imine lassen sich durch Nitrosierung der entsprechenden Sydnon-imin-Hydrochloride erhalten, dabei konnen beide Reaktionsschritte, Bildung des Sydnon-imin-Hydrochlorids und Nitrosierung, als Eintopfreaktion durchgefuhrt werden. Beim Erwarmen werden diese unter Stickstoff-Eliminierung in die Sydnone ubergefuhrt. 

Rl R2. .. -sydnon-imin-Hydrochlorid [%] Schmp. [°C] Lite- ratur... 

The arylmethylene imine hydrochloride 2 was sampled under dry argon, precisely weighed (ca. 2 mmol) and ball-milled with the equivalent of 2-naphthol 1 for 1 h. The solid-solid character was finally lost during the reaction as the material became sticky. The free base 3 was obtained after neutralization of 3 HC1 in CH2C12 by washing with NaHC03 solution and crystallization from ethanol. 

Crystalline derivatives of aliphatic nitriles may be prepared by an application of the Hoesch reaction. Equimolecular proportions of phloroglucinol and the nitrile react in dry ethereal solution in the presence of anhydrous zinc chloride and hydrogen chloride to give an imine hydrochloride, which is converted into a solid alkyl trihydroxyphenyl ketone by hydrolysis. The alkyl 2,4,6-trihydroxy-phenyl ketones are usually highly crystalline solids of sharp melting point and are purified by recrystallisation from hot water. Many contain water of crystallisation which can be removed by drying in vacuo at about 100 °C the melting points of both the hydrated and anhydrous compound should be determined. 

Methylbenzo-1,4-thiazin-3(4//)-imine hydrochloride (132) with acetic anhydride gave the hexacyclic product (133) (neat reactants, reflux, 90 min 57%), which underwent desulfurization by Raney nickel to afford 4,5-dimethyl-2,7-bis(/V-methylanilino)-1,6-naphthyridine (134) (PhH, reflux, 12 h 20%).1032... 

SYNS ADC AURAMINE O AIZEN AURAMINE AURAMINE (MAK) AURAMINE HYDROCHLORIDE AURAMINE O (BIOLOGICAL STAIN) AURAMINE YELLOW 4,4 -BIS(DIMETHYLAMINO)BENZHYDRY-LIDENIMNE HYDROCHLORIDE 4,4 -BIS(DI-METH T..AMINO)BENZOPHENONE-IMINE HYDROCHLORIDE l,l-BIS(p-DIMETHYLAMINO-PHEN T)METHYLENIMINEHYDROCHLORlDE CALCOZINE YELLOW OX 4,4 -CARBONIMIDOYL-BIS(N,N-DIMETHYI.BENZENAMINE)MONOHYDRO-CHLORIDE C.I. 41000 0 C.I, BASIC YELLOW 2 C.I. BASIC YELLOW 2, MONOHYDROCHLORIDE MITSUI AURAMINE O... 

BISpiMETHYLAMINO)BENZOPHENONE-IMINE HYDROCHLORIDE see IBAOOO BIS(piMETHYLAMINO)CARBONOTHIOYL) DISULPHIDE see TFS350... 

The Schmitz reaction can be unsuccessful in sterically demanding environments in such circumstances, the electrophilic aminating agent reacts faster with ammonia than with hindered ketones <1965JA2665>. Consequently, the synthesis of 2-azi-camphane 64, a compound which is unobtainable under standard conditions <1996TL6647>, was achieved by slow diaziridination of camphor imine hydrochloride 63 (rather than camphor itself) with hydroxylamine-O-sulfonic acid (HOSA)-ammonia, followed by iodine-mediated oxidation (Scheme 22) <2001S379>. 

Concrete evidence for the existence of a cyclic intennediate of the type postulated by Van Tamelen, and also by Harding and oo-workors, - was sought by Price and KirlL with propyJeiie oxide. Careful treatment of l>thjo< anatc-2-prupanol with hydrogen chloride yielded a salt for U hich the t olic imine hydrochloride structure shown in Eq (67C) was formulated. Conversion of this salt into i[Pg.447]

The mechanisms of the Gattermann and Gattermann-Koch formylation belong to the category of electrophilic aromatic substitution (SEAr) but are not known in detail, since they have a tendency to vary from one substrate to another, and the reaction conditions may also play a role. When carbon monoxide is used, the electrophilic species is believed to be the formyl cation, which is attacked by the aromatic ring to form a -complex. This -complex is then converted to the aromatic aldehyde upon losing a proton. When HCN is used, the initial product after the SEAr reaction is an imine hydrochloride, which is subsequently hydrolyzed to the product aldehyde. 

Oxatriazolium-5-aminides (9) are structurally related to sydnon-imines (3). As with sydnonimines, the 5-imine derivatives are stable only as salts or in their N-acylated forms. 3-Cyclohexyl-1,2,3,4-oxatriazole-5-imine hydrochloride was first synthesized by Finnegan and Henry in 1965 [55]. The biological activity was reported by Masuda et al. in 1971 [56]. Oxatriazole-5-imines (9) have been reported to be an important class of NO donors and potent antiplatelet, fibrinolytic, thrombolytic, and bronchiectatic agents [57]. However, an extensive investigation of the NO-releasing and other biologi-... 

Ai-Aryl nitrones combine rapidly with phosgene to give imine hydrochlorides that are chlorinated in the ring (predominantly at the 2- position). Reaction occurs at room... 

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