2-Imidazoline,2- 2- ethyl

Carbimazole. 2,3-Dihydro-3-mrthyi-2-thioxo-lH-imidazole-l-carboxylic acid ethyl ester, l-ethoxycarbonyl-3-methyl -2-thio-4-imidazoline ethyl 3 -methyl -2 -thioimid azoline-1 -carboxylate 1 -methyl -3-carbethoxy-2-thiogly-oxalone athyromazole Neo-mercazole Neo-Thyreostat. C,H10N2OjS mol wt 186.23. C 45.15%, H 5.417=, N 15,047=., O 17.187=, S 17.22%. Prepn RimingtOn et al,... 

Chemical Name 2-[1-(2,6-Dichlorophenoxy)ethyll-2-imidazoline Common Name -... 

After cooling, unreacted ethylenediamine is neutralized in a cooling mixture with the absolute ethanolic hydrochloric acid, filtered off from any components that are insoluble in ethanol and approximately two-thirds of the solvent filtered off under suction in a water jet pump vacuum. Residual quantities of ethylenediamine dihydrochloride are precipitated in fractions by the careful addition of ethyl methyl ketone, after which the imidazoline hydrochloride is separated off by the addition of dry ether. Following repeated recrystallization from ethanol ether, 2-[0(-(2,6-dichlorophenoxy)ethyl] -A -imidazoline hydrochloride is obtained in the form of small white crystals melting at 221°C to 223°C. 

Aziridines have been synthesized, albeit in low yield, by copper-catalyzed decomposition of ethyl diazoacetate in the presence of an inline 260). It seems that such a carbenoid cyclopropanation reaction has not been realized with other diazo compounds. The recently described preparation of 1,2,3-trisubstituted aziridines by reaction of phenyldiazomethane with N-alkyl aldimines or ketimines in the presence of zinc iodide 261 > most certainly does not proceed through carbenoid intermediates rather, the metal salt serves to activate the imine to nucleophilic attack from the diazo carbon. Replacement of Znl2 by one of the traditional copper catalysts resulted in formation of imidazoline derivatives via an intermediate azomethine ylide261). 

Tolazoline Tolazoline, 2-benzyl-2-imidazoline (12.2.7), is synthesized by the heterocy-clation of the ethyl ester of iminophenzylacetic acid with ethylendiamine (12.2.6), which forms the desired product (12.2.7) [32-35]. The structure of tolazoline is strikingly similar to a-adrenergic agonists, which are antiedema sympathomimetics. 

Als Nebenprodukte entstehen oft 1,3-Oxazole (vgl. Bd. E8a, S. 903, 911). a-Hydroxy- und a-Acetoxy-ketone liefern die entsprechenden 1,3-Oxazole sogar als Hauptprodukte42,43. Aus 3-Brom-l-oxo-l-phenyl-butan erhalt man mit Ammoniumformiat in Ameisensaure 4-Ethyl-5-phenyl-imidazolin 75% Ausbeute. Dagegen entsteht aus dem isomeren l-Brom-2-oxo-l-phenyl-butan unter analogen Reaktionsbedingungen das entsprechende 1,3-Oxazol in iiber 70% Aus-... 

McKay,JOC 16,1846-50(1951) CA 46, 9096—7(1952) (Reactions of ethyl amine and p-aminoacetanilide with l-nitroso-2-nitramino -AI-imidazolxne) 5)A.F.McKay, CanjChem 31,284-6(1953) CA 48,153(1954) (Reaction of mechylamine with i-nitroso-2-nitramino-Aa-imidazoline)... 

N tr ami no- A4 i mi da zol i n-1- yl)et hyl]-3 -nitro-1 -nitroso-guanidi ne 1-[j8 3 -Nitro-1 nitro s guanidino)ethyl]-2-nit rami no-A4-imidazofine or l-(N-Nitroguanyl-N -nitroso-jg-am inoethyl)-2-nitromino-Al-imidazoline,... 

Aminoimidazolin-l-yl and derivs 1 A222—A223 1 -[2-(2-nitramino-A2 -imidazolin-1 -yl) ethyl] -... 

I -[)3-(2 Nitramino-A2-imidazolin-l-yl)ethyl]-3 -nitro-1 -nitroso-guanidine 1-[j0-(3 -Nitro-l -nitrosoguanidino)ethyl]-2-nitranino-A2-imidazoline or l-(N-Nitroguanyl-N -nitroso-/3-am inoethy l)-2-nitron ino-A2-i mid azoline,... 

See Acetaldehydepicrylhydrazone A15-L TEthyl-2-nitramino-Aa-imidazoline A220-R 1-Ethyl-2-nitrimino-3-nitroimidazolidine... 

The Lewis acid-catalysed 3 + 2-cycloaddition of aziridine-2-carboxylates with isocyanates proceeds regio- and stereo-specifically to produce enantiomerically pure 4-substituted imidazolin-2-ones in high yields.33 The reaction of ethyl 7-iodo-2-heptynoate (27), 2-arylaziridines (28), and K2C03 produces polysubstituted indolizidines (30) via an S /formal 3 + 2-cycloaddition (29) process (Scheme 8).34... 

The ethyl ester of 1-aminocyclopentanecarboxylic acid (1.57 g) and ethyl valerimidate (1.56 g) are dissolved in 12 ml of xylene containing 6 drops of acetic acid. After refluxing for 6.5 h, the reaction medium is concentrated under vacuum, the residue is chromatographed on silica gel using a chloroform/methanol/acetic acid mixture (94/4/2 v/v/v) as the eluent. The fraction containing the expected product is evaporated several times in the presence of xylene and then benzene in order to remove the acetic acid. 1.91 g of 2-n-butyl-4-spirocyclopentane-2-imidazolin-5-one are obtained in the form of a thick oil. 

A mixture containing 250 mg of sodium hydride (as an 80% dispersion in mineral oil) and 5 ml of DMF is prepared under a nitrogen atmosphere and a solution containing 0.97 g of 2-n-butyl-4-spirocyclopentane-2-imidazolin-5-one in 10 ml of DMF is added dropwise. The mixture is stirred for 30 min at 20°C and a solution of 1.5 g of 4-bromomethyl-2 -cyanobiphenyl in 10 ml of DMF is then added. After stirring for 1 h at 20°C, the DMF is evaporated off under reduced pressure, the residue is then taken up with ethyl acetate. 

Chemical Name 2-[l-(2,6-Dichlorophenoxy)ethyl]-2-imidazoline hydrochloride... 

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