Formamidine hydrochloride

CH4N2 463-52-5) see Itraconazole formamidine hydrochloride (CH5QN2 6313-33-3) sec Allopurinol 7-formamidocephalosporanic acid (CiiHj2N20fiS 27267-35-2) see Cefamandole 2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetic acid (C7H7N3O4S 83594-38-1) see Ceftizoxime (2-formamidothiazol-4-yl)oxoacetic acid (CfiH4N204S 64987-06-0) see Cetixime formic acid... 

Auch das einfachste Amin, Ammoniak, geht diese Reaktion ein (24), doch ist die Anwesenheit von HC1 zwecks Abfangens des Formamidin-hydrochlorids angebracht, so daB man in diesem Falle zweckmaBig NH3 in Form von Ammoniumchlorid einsetzt (27). 

The 6-benzylpyrido[4,3-, pyrimidine 145 was prepared by cyclizing the methyl carboxylate 612 with formamidine hydrochloride <2000DEP19900544>. The 2-butyl-6-(2-hydroxy-2-methyl-l-oxopropyl) analogue 615 was also prepared from cyclocondensation of ethyl ester 613 with BuC(NH)NH2 <1994USP5281602>. The trisubstituted analogue 616 was obtained from the reaction of 2-guanidino-4-(4-fluorophenyl)thiazole hydrobromide with iV,3-dibenzoyl-4-piperidone 614 <1995USP5405848>. 

Because formamidine hydrochloride is extremely deliquescent, considerable care must be exercised in its preparation if satisfactory results are to be achieved. Furthermore, formamidine hydrochloride cannot be used directly in most condensation reactions it must be treated first with a mole of base to liberate free formamidine. The same restriction applies to the metho-sulfate salt of formamidine in addition, complications in synthesis may be anticipated in this latter case because methyl hydrogen sulfate itself is an effective methylating agent.6... 

ENT 27,567 EP-333 FUNDAL FUNDAL 500 FUNDEX GALECRON N -(2-METHYL-4-CHLOROPHENYL)-N,N-DIMETHYLFORMAMIDINE N -(2-METHYI 4-CHLORPHENYL)-FORMAMIDIN-HYDROCHLORID (GERMAN) NSC-190935 RS 141 SCHERING 36268 SN 36268 SPANON SPANONE... 

In the absence of a base a different reaction occurs, and formamidine hydrochlorides XXXIV are isolated (I36.i66,i69.i70,241.294)... 

Reaction of CXCI with 4-aminoazobenzene results in the formation of N,N-dimethyl-N -(4-phenylazophenyl)formamidine hydrochloride... 

The use of carbonyl chloride in the conversion of thioureas to chloro-formamidines offers the advantage of gaseous by-product. Phosphorus pentachloride can be used equally well, but complete separation from the liquid trichlorophosphorus sulfide is sometimes more difficult to accomplish. In one instance, chlorine has been used to convert a pseudothiourea derivative to the corresponding chloroformamidine hydrochloride. Thus, addition of chlorine to a solution of the pseudothiourea derivative XIII in carbon tetrachloride afforded a quantitative yield of trimethylchloro-formamidine hydrochloride (XIV) C ). 

Likewise, heating of an equimolar mixture of N,N -dicyclohexylchloro-formamidine hydrochloride (LXIV) and 1,3-dicyclohexylurea (LXV) produces N,N, N"-tricyclohexylguanidine hydrochloride (LXVI) in high yield... 

Reaction of mesoionic l,3-oxazolium-5-olates with amidines afforded 5-(tri-fluoroacetyl)imidazoles (Scheme 38) [52], The mechanism for this novel ring transformation is presumably initiated by the nucleophilic attack of amidines onto C-2 of l,3-oxazolium-5-olates. Subsequent ring fragmentation followed by decarboxylation and recyclization of the enolate ion with concomitant loss of ammonia afforded 5-trifluoroacetylated imidazoles. Reaction of iV-benzoyl-Af-methylglycine with pentafluoropropionic anhydride or heptafluorobutyric anhydride followed by the treatment of the resulting l,3-oxazolium-5-olates with formamidine hydrochloride also afforded the corresponding 5-perfluoroacylimid-azoles in an one-pot fashion. 

A rapid stream of dry NH3 passed into a boiling mixture of ethyl orthoformate and moles of glacial acetic acid for 45 min., and the resulting ethanol slowly distilled at an oil-bath temp, of 155-160° until after ca. 30 min. the temp, of the condensing vapor drops below 75° formamidinium acetate. Y 84.2%.— The product may be used directly in many condensation reactions without prior liberation of free formamidine. It may also be used in place of formamidine hydrochloride. Also acetamidinium acetate s. E. G. Taylor and W. A. Ehrhart, Am. Soc. 82, 3138 (1960). 

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