1 -Methyl-imidazoline-2

Imidazole nitrones 127 reacted with dimethyl acetylenedicarboxylate to yield imidazo[l,5-fc]isoxazoles 128, which in the presence of base afforded imidazoles 129 <00TL5407>. Chiral imidazoline nitrone 130 participated in a [3+2] cycloaddition reaction with various dienophiles to furnish imidazoisoxazoles 131 <00SL967>. A convenient synthesis of AyvyV -trisubstituted ethylenediamine derivatives from 2-methyl-2-imidazoline has been reported <00SC3307>. Dehydrogenation of 1,3-di- and 1,2,3-trisubstituted imidazolidines afforded l//-4,5-dihydroimidazolium salts <00SC3369>... 

Exposure of 2-methyl-2-imidazoline to a mixture of nitric and acetic acids leads to both oxidation and nitration, giving l,3-dinitroimidazolidin-2-one (179). When 2-nitramino-2-imidazolines are further nitrated they give the 1-nitro products (176) which are dinitroguanidines. Addition of amines and alcohols leads to (177) and (178), respectively, while allylic rearrangement followed by further nitration gives (179 Scheme 86). 

To 2-methyl-2-imidazoline (0.5 g, 5.95 mmol) dissolved in dry dioxane (15 ml) under nitrogen is added, in small portions with stirring, potassium permanganate (1.5 g, 9.5 mmol). The mixture is then refluxed (12 h), allowed to cool to room temperature, and filtered through Celite. The filtrate is evaporated under reduced pressure to a yellowish solid, which is recrystallizcd from toluene (0.352 g, 72%), m.p. 140-142°C. Similar dehydrogenations of the 2-ethyl-and 2-propyl-2-imidazolines were accomplished with 48 and 50% efficiencies, respectively. 

N-Alkylation of 2-methyl-2-imidazoline can be achieved under phase transfer catalysis. The reaction works best with mixed bases in the absence of a solvent (Scheme 137 R Et, Pr, Bu, CyHis, C12H2S yields 60-96%) <1999SC3025>. 

When V-substituted 2-methyl-5-nitroimidazoles (46) are photolyzed in the presence of water the first products are 2-methyl-2-imidazoline-4,5-dione-4-oximes. This transformation follows the... 

As mentioned above a 2-methylene group in quaternary salts, or even in compounds like I-benzyl-2-methyl-2-imidazoline (133), can be deprotonated by reagents like butyllithium or sodium hydride. When there is no A-substituent only A//-deprotonation occurs even with excess butyl-lithium. By use of the reaction sequence shown in Scheme 65 an electrophile can be introduced both at the annular nitrogen and on the 2-methyl group <90JCS(Pl)375>. 

Beilstein Handbook Reference) A13-16865 BRN 0104225 4,5-Dihydro-2-methyl-1H-imidazole EINECS 208-596-6 IH-lmidazole, 4,5-dihydro-2-methyl- 2-Imidazoline, 2-methyl- Lysidine Methylglyoxalidine 2-Methyiimidazoline. Crystals mp 107° bp = 196.5° insoluble in EI2O, soluble in CHCI3, very soluble in H2O, EtOH. 

Biimidazole (3). 2,2 -Bi(2-imidazoline) (1) can be oxidized to 2,2 -biimidazole (3) by conversion to the bistrimethylsilyl derivative (2), which is soluble in organic solvents, and oxidation of (2) in CCI4 with the activated manganese dioxide of Goldman (2, 257). The procedure can also be used to oxidize 2-methyl-2-imidazoline to 2-methylimidazole (67% overall yield). ... 

Methyl-2-hexyne, 178 Methylhydrazine, 281 Methyl hypobromite, 72 2-Methylimidazole, 357 2-Methyl-2-imidazoline, 357 1-Melhylindenes, 468 Methyl iodide, 384... 

Hydrolysis in aqueous ethanol of 2-methyl imidazolines 561, derived from C2-symmetric diamines and the Pinner salt, leads to mono-protected 1,2-diamines 562. The latter are readily converted into A, A -disubstituted 1,2-diamines (Scheme 131) <2000TL8431>. N-protected A -imidazolines are readily hydrolyzed under milder conditions. Thus peptidyl trifluoromethyl ketones 564 were prepared through hydrolysis of 563 <1996JA8485>. 

Dialkoxylated alkylpolyoxy alkylamine Product of 4,4 -thiodiphenol, formaldehyde and cocoamines Reaction products of hydroxyl-methyl imidazoline and acyl sarcosine Salts of imidazolines... 

Fats, Oils, or Fatty Acids. The primary products produced direcdy from fats, oils, or fatty acids without a nitrile iatermediate are the quatemized amidoamines, imidazolines, and ethoxylated derivatives (Fig. 3). Reaction of fatty acids or tallow with various polyamines produces the iatermediate dialkylarnidoarnine. By controlling reaction conditions, dehydration can be continued until the imidazoline is produced. Quaternaries are produced from both amidoamines and imidazolines by reaction with methyl chloride or dimethyl sulfate. The amidoamines can also react with ethylene oxide (qv) to produce ethoxylated amidoamines which are then quaternized. 

Another class of herbicides, the imida zolines, was discovered at American Cyanamid in the early 1980s. Extensive research has led to the development of four commercial compounds imazapyr, imazamethahenz-methyl, imazethapyr, and imazaquin (see Table 5). Like the sulfonylureas, the imidazolines are extremely active at low rates. 

Fabric Softeners, Surfactants and Bleach Activators. Mono- and bisamidoamines and their imidazoline counterparts are formed by the condensation reaction of one or two moles of a monobasic fatty acid (typically stearic or oleic) or their methyl esters with one mole of a polyamine. Imidazoline formation requires that the ethyleneamine have at least one segment in which a secondary amine group Hes adjacent to a primary amine group. These amidoamines and imidazolines form the basis for a wide range of fabric softeners, surfactants, and emulsifiers. Commonly used amines are DETA, TETA, and DMAPA, although most of the polyethylene and polypropane polyamines can be used. 

Many of the surfactants made from ethyleneamines contain the imidazoline stmcture or are prepared through an imidazoline intermediate. Various 2-alkyl-imidazolines and their salts prepared mainly from EDA or monoethoxylated EDA are reported to have good foaming properties (292—295). Ethyleneamine-based imida zolines are also important intermediates for surfactants used in shampoos by virtue of their mildness and good foaming characteristics. 2- Alkyl imidazolines made from DETA or monoethoxylated EDA and fatty acids or their methyl esters are the principal commercial intermediates (296—298). They are converted into shampoo surfactants commonly by reaction with one or two moles of sodium chloroacetate to yield amphoteric surfactants (299—301). The ease with which the imidazoline intermediates are hydrolyzed leads to arnidoamine-type stmctures when these derivatives are prepared under aqueous alkaline conditions. However, reaction of the imidazoline under anhydrous conditions with acryflc acid [79-10-7] to make salt-free, amphoteric products, leaves the imidazoline stmcture essentially intact. Certain polyamine derivatives also function as water-in-oil or od-in-water emulsifiers. These include the products of a reaction between DETA, TETA, or TEPA and fatty acids (302) or oxidized hydrocarbon wax (303). The amidoamine made from lauric acid [143-07-7] and DETA mono- and bis(2-ethylhexyl) phosphate is a very effective water-in-od emulsifier (304). 

Imidazolidin-2-one, l-(5-nitro-2-thiazolyl)-pharmacological activity, 6, 328 Imidazolidin-4-one, l-aryl-3-phenyl-2-thioxo- C NM S, 355 Imidazolidinones C NMR, 5, 355 Imidazolidin-2-ones nucleophilic displacement, 5, 428 polymers, 1, 279-280 reactivity, 5, 376 synthesis, 5, 466, 471 Imidazolidin-4-ones synthesis, 5, 468 Imidazoline, 2-alkyl-synthesis, 5, 463 Imidazoline, 2-amino-applications, 5, 498 Imidazoline, 2-aryl-synthesis, 5, 463 Imidazoline, 2-methyl-synthesis, 5, 487 Imidazoline, 2-nitroamino-synthesis, 5, 471 2-Imidazoline, 2-arylamino-tautomerism, 5, 368 2-Imidazoline, 1-benzyl-methylation, 5, 425 2-Imidazoline, 1,2-diaryl-synthesis, 5, 463... 

Imidazoline-2-thione, 4,5-diphenyl-oxidation, 5, 405, 445 Imidazoline-2-thione, 4-methyl-Mannich reaction, S, 405 oxidation, 5, 445... 

Imidazolin-5-one, 2-methyl- H NMI 5, 354 2-Imidazolin-5-one, 2-phenyl-reactivity, 5, 376 synthesis, 5, 479... 

Imidazolin-2-one, 1,5-diphenyl-4-aryl-synthesis, 5, 492 4-Imidazolin-2-one, 1-hydroxy-synthesis, 5, 474—475 4-Imidazolin-2-one, l-methyl-3-phenyl- C NMR, 5, 355 Imidazolinones acylation, 5, 424, 443 alkylation, 5, 443 developers... 

However, the thione form of mereaptoazole ligands is retained in the metal eomplexes of l-methyl-l,3-imidazolin-2-thione 370 (90POL981) and 371 [92ICA75 93JOM(453)47], l-phenyltetrazol-5-thione 372 [96JOM (513)63] and l,3-thiazolidin-2-thione 373 (89ICA265). 

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. 

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