59639-25-7

Upstream product

• 59639-21-3 1-(4-chloro-α-phenyl-o-tolyl)imidazole 
• 61875-59-0 N-(2-Benzyl-4-chloro-phenyl)-formimidic acid ethyl ester 
• 40545-76-4 2-Amino-5-chlordiphenylmethan 

Downstream Products

• 121898-97-3 7-Chloro-9-phenyl-9H-imidazo[1,2-a]indol-9-ol 
• 59678-87-4 5-chloro-2-(2-hydroxymethylimidazol-1-yl)benzophenone 
• 121898-98-4 7-Chloro-3-dimethylaminomethyl-9-phenyl-9H-imidazo[1,2-a]indol-9-ol 
• 54534-20-2 5-chloro-2-(2-dimethylaminomethyl-imidazol-1-yl)-benzophenone 
• 57166-52-6 2-imidazol-1-yl-5-nitro-benzophenone 
• 121899-01-2 7-chloro-9-<2-(dimethylamino)ethoxyl>-9-phenyl-9H-imidazo<1,2-a>indole 

Relevant academic research and scientific papers

Mannich Reactions of Heterocycles with Dimethyl(methylene) Ammonium Chloride: A High Yield, One-step Conversion of Estazolam to Adinazolam

The readily prepared ammonium salt, (CH3)2N=CH2(1+)*Cl(1-), 4, functionalized heterocycles differently, but in a predictable fashion, under neutral, basic or acidic conditions.Triazolo- and imidazobenzophenones 1b' and 5, which primarily underwent intramolecular isomerization to indolols 2a' and 6a rather than intermolecular electrophilic substitution under conditions of the normal aqueous Mannich reaction, were converted with 4 to the desired benzophenone derivatives, 1c' and 7, respectively, in moderate yields.The 1-unsubstituted triazolo- or imidazobenzodiazepines, 10a estazolam and 10b, were transformed to the corresponding 1-(dimethylamino)methyl derivatives, 11a (adinazolam) and 11b, in good to moderate yields (61percent and 32percent, respectively.) Under acidic reaction conditions, 1-methyl triazolobenzodiazepine, 10d (alprazolam), afforded 12e, the product of attack at C-4 of the triazolobenzodiazepine ring system.Under strongly basic conditions in which the anion of 10d was generated prior to reaction with 4, both 12e and its isomer, 15, were formed.These results complement the report that 4 may be used to functionalize the 1-methyl position of triazolobenzodiazepines, and further demonstrate the versatility of reagent 4 in heterocyclic synthesis.

2-(Imidazol-1-yl)benzophenones

Compounds of the formulae IV and V: SPC1 wherein Ro and R1 are hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; wherein R2 is hydrogen, fluoro, chloro, or trifluoromethyl; wherein R3 is hydrogen or fluoro with the proviso that R3 cannot be fluoro, if R2 is chloro or trifluoromethyl; and wherein R4 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro, are obtained by a multi-step reaction from the corresponding α-(phenyl)-o-toluidine of the formula I SPC2 wherein R2, R3, and R4 are defined as above, by treating I in sequence with an alkyl ester of orthoformic acid the resulting product with 2-alkyl-2-(aminoalkyl)-1,3-dioxolane or a 2-amino-alkanone dialkyl ketal and finally with titanium tetrachloride to obtain compound IV, and oxidizing compound IV to obtain the corresponding compound V. Compounds IV and V have minor tranquilizing activity which can be utilized to calm mammals or birds. Their more important use, however, is as intermediates in the production of the strongly sedating and tranquilizing imidazolobenzodiazepines.