2- imidazoline 2-alkyl

Industrial surfactants find uses in almost every industry, from asphalt manufacturing to carpet fibers, from pulp and paper production to leather processing. Examples of the types of chemicals used as surfactants are fatty alcohol sulfates, alkanolamides, alkoxylates, sulfosuccinates, amines, quaternaries, phosphate esters, acid esters, blockcopolymers, betaines, imidazolines, alkyl sulfonates, etc. 

Fig. 3. Quatemaiies fiom amidoamines and imidazolines where R is a fatty alkyl group.

In addition to the mono- and dialkylamines, representative stmctures of this class of surfactants include /V-alkyltrimethylene diamine, RNH(CH2)3NH2, where the alkyl group is derived from coconut, tallow, and soybean oils or is 9-octadecenyl, 2-aLkyl-2-imidazoline (3), where R is heptadecyl, heptadecenyl, or mixed alkyl, and l-(2-aniinoethyl)-2-aLk5l-2-imidazoline (4), where R is heptadecyl, 8-heptadecenyl, or mixed alkyl. 

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-4-thione, 4,4-diaryl-rearrangement, S, 376 2-Imidazoline-4-thione, 5,5-diaryl-rearrangement, S, 376 2-Imidazoline-4-thione, 5,5-diphenyl-aromatization, 5, 422 2-Imidazoline-5-thione, 4,4-diaryl-rearrangement, 5, 376 2-Imidazoline-5-thione, 5,5-diaryl-rearrangement, S, 376 Imidazolinethiones acylation, S, 424 alkylation, S, 444 C NMR, S, 355... 

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... 

As yet, a number of experiments have failed to convert ureas 205 such as N-phenylurea or imidazolin-2-one by silylation amination with excess amines R3NHR4 such as benzylamine or morpholine and excess HMDS 2 as well as equivalent amounts of NH4X (for X=C1, I) via the silylated intermediates 206 and 207 in one reaction step at 110-150°C into their corresponding guanidines 208 with formation of NH3 and HMDSO 7 [35] (Scheme 4.13). This failure is possibly due to the steric repulsion of the two neighbouring bulky trimethylsilyl groups in the assumed activated intermediate 207, which prevents the formation of 207 in the equilibrium with 206. Thus the two step Rathke-method, which demands the prior S-alkylation of 2-thioureas followed by amination with liberation of alkyl-mercaptans, will remain one of the standard syntheses of guanidines [21, 35a,b,c]. 

The foam-holding characteristics of foam from surfactants in oil field jobs can be tailored by adding an imidazoline-based amphoacetate surfactant. Amphoacetates are a special class of amphoteric tensides (Figure 16-1). Imidazoles, such as 2-heptylimidazoline, are reacted with fatty acids under the ring opening. For alkylation, the imidazoline is reacted with, for example, chloroacetate [493]. 

Interposition of an oxygen atom between the aromatic ring and the imidazoline-bearing side chain leads to a compound reported to show antidepressant activity. Its preparation begins with alkylation of phenol 125 with chloroacetonitrile to afford intermediate 126. Condensation of that nitrile with the... 

Preparation of a rather more complex imidazoline drug starts with the alkylation of the carbanion from p-chlorophenylacetonitrile (128) with 2-bromopyridine. Reaction of the product (129) with ethylenediamine serves to form the imidazoline ring (130). Air oxidation then affords the tertiary carbinol by attack at the highly activated, multiply benzylic carbon. There is thus obtained the antidepressant dazadrol (131).31... 

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). 

Imidazolines are also formed in silver cyanide-catalyzed cyclization of alkyl isocyanides with aliphatic diamines (Scheme 103).169 This simple synthesis can be applied in a general way with difunctional nucleophiles and has been used to prepare benzimidazoles, oxazoles, thiazoles, and oxazines.169 It is suggested that transient carbene complexes are formed in these reactions (cf. 87 in Scheme 103) but further work is required to ascertain the mechanism and scope of these processes. 

The N-trichloroacetyl cyclopropenone imine 424 reacts with 3-aroyl- or 3-carbe-thoxy-N-alkyl aziridines exclusively across the C=N bond giving rise to spirocyclo-propenes 425 and the imidazoline 426267 ... 

This procedure was utilized by the same authors to synthesize a large library of 4-carbohydroxamido-2-(aryl or alkyl)-2-imidazolines, some of which exhibited excellent LpxC inhibitory and antibacterial activities. The technical maneuvers in the syntheses of these compounds and their structure-activity relationships are comprehensively covered by the authors in their paper. 

By using diamines, the 2-alkyl-(benzo)imidazolines 581 and 582 were formed by a double Michael addition reaction and subsequent elimination of MeCN [266, 267]. 

Figure 21. Substitution of alkyl groups in the phenyl ring in imino— imidazolines and effect on blood pressure...

One type of cationic surfactant was the fatty acid derivatives of polyamines. The properties of the derivatives of fatty acids and ethylenediamine have been described in the literature (7-9). It appeared from these reports that the 2-alkyl-2-imidazolines would not impart sufficient hydrophobicity to soils. However, the analogous series of homologous compounds from the fatty acids and diethylene-triamine (BETA) appeared likely to do so because of their higher molecular weight. 

For example, complex 37 with an imidazolin-2-ylidene and a methyl ligand in cis-position to each other decomposes to yield the 1,2,3-trimethylimidazolium salt 38, Pd°, and cod (Fig. 13) [124], Additional examples for the reductive elimination of 2-alkyl and 2-aryl substituted azohum salts from palladium or nickel NHC complexes have been reported [125, 126]. Today, reductive elimination reactions have been established as one important reaction pathway for the deactivation of catalytically active metal NHC complexes [126, 127]. 

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