Ethanolamine, reaction with

Reaction of dibenzylamine with ethylene oxide affords the amino alcohol, 82. Treatment of that product with thionyl chloride gives the a-sympathetic blocking agent, dibenamine (83). (Condensation of phenol with propylene chlorohydrin (84) gives the alcohol, 85. Reaction with thionyl chloride affords the chloride (86). Use of the halide to alkylate ethanolamine affords the secondary amine (87). Alkylation of this last with benzyl chloride... 

Sheratte55 reported the decomposition of polyurethane foams by an initial reaction with ammonia or an amine such as diethylene triamine (at 200°C) or ethanolamine (at 120°C) and reacting the resulting product containing a mixture of polyols, ureas, and amines with an alkylene oxide such as ethylene or propylene oxide at temperatures in the range of 120-140°C to convert the amines to polyols. The polyols obtained could be converted to new rigid foams by reaction with the appropriate diisocyanates. 

The synthesis of ethylenediamine (EDA) from ethanolamine (EA) with ammonia over acidic t3pes of zeolite catalyst was investigated. Among the zeolites tested in this study, the protonic form of mordenite catalyst that was treated with EDTA (H-EDTA-MOR) showed the highest activity and selectivity for the formation of EA at 603 K, W/F=200 g h mol, and NH3/ =50. The reaction proved to be highly selective for EA over H-EDTA-MOR, with small amounts of ethyleneimine (El) and piperazine (PA) derivatives as the side products. IR spectroscopic data provide evidence that the protonated El is the chemical intermediate for the reaction. The reaction for Uie formation of EDA from EA and ammonia required stronger acidic sites in the mordenite channels for hi er yield and selectivity. 

An important feature of the antibiotic chloramphenicol (9) is the presence of the dichloroacetamide function. Inclusion of this amide in a simpler molecule, teclozan (15), leads to a compound with antiamebic activity. Whether this is cause and effect or fortuitous is unclear. The synthesis begins with alkylation of the alkoxide derived from ethanolamine (10) with ethyl iodide to give the aminoether (11). Reaction of a,a -dibromo-p-xylene (12) with 2-nitropropane in the presence of base leads to dialdehyde (13). The reaction probably proceeds by O-alkylation on the nitropropyl anion... 

The method can be used for the synthesis of functionalized isocyanide complexes, e.g., reaction with ethanolamine produces a 2-hydroxy-ethylisocyanide complex,... 

N-2-Chloroethylfluoroacetamide was also prepared by the direct action of 2 mol. of fluoroacetyl chloride on ethanolamine, although we carried out this reaction with the intention of preparing 2-(fluoroacetamide)ethyl fluoroacetate,... 

Optically pure P-ethanolamines react with dichlorocarbene under phase-transfer catalytic conditions to produce epoxides of high configurational retention [30]. Initial reaction occurs at the tertiary nitrogen centre (Scheme 7.29) with subsequent cleavage of the C-N bond. The reaction is configurationally controlled, as shown by the reaction of the conformationally rigid cyclic systems epoxide formation occurs with the equatorial hydroxyl system (50%), but not with the axial hydroxyl compound. 

Acetylcholine Acetylcholine, 2-acetoxy-A,A,A-trimethylethyl ammonium chloride (13.1.2), is easily synthesized in a number of different ways. For example, 2-chloroethanol is reacted with trimethylamine, and the resulting A,A,A-trimethylethyl-2-ethanolamine hydrochloride (13.1.1), also called choline, is acetylated by acetic acid anhydride or acetylchloride, giving acetylcholine (13.1.2). A second method consists of reacting trimethylamine with ethylene oxide, giving A,A,A-trimethylethyl-2-ethanolamine hydroxide (13.1.3), which upon reaction with hydrogen chloride changes into the hydrochloride (13.1.1), which is further acetylated in the manner described above. Finally, acetylcholine is also formed by reacting 2-chloroethanol acetate with trimethylamine [1-7]. 

Lomustine Lomustine, l-(2-chloroethyl)-3-cyclohexyl-l-nitrosourea (30.2.4.3), is made by reacting ethanolamine with cyclohexylisocyanate, which forms l-(2-hydroxyethyl)-3-cyclohexylurea (30.2.4.1). Upon reaction with thionyl chloride, the hydroxyl gronp in it is replaced with a chlorine atom, giving l-(2-chloroethyl)-3-cyclohexylurea (30.2.4.2). This is nitrated in non-aqueons conditions with formic acid and sodinm nitrite to give lomustine (30.2.4.3) [67,68]. 

In contrast to NjPjCle, N4P4Q8 is extremely reactive towards difunctional reagents. This has led to the isolation of several decomposition products. Reactions with Af-methyl ethanolamine [87], 1,3-propane diol and 1,3-diamino propane afford mainly spiro products [138]. A detailed investigation on the reactions of N4P4CI8 with HO- CH2) -OH (n = 3, 4) has revealed that... 

Other approaches to pyrimido[4,5- ][l,4]oxazines include the reaction of an ethanolamine derivative with a halopyrimidin-4-ol (Scheme 83), followed by ring closure <2006TL4437>. Formation of a pyrimido[4,5- ][l,4]-oxazine is also a competing reaction in a reported approach to pteridines (Equation 147) <1996T13017>. 

Fig. 5. The reaction of ethanolamine-phosphate cytidylytransferase with substrates and analogues. Reaction 1 shows the normal reaction of the enzyme with ethanolamine phosphate (2-aminoethyl phosphate), which is part of the route of phospholipid synthesis. The alternative reaction with 2-aminoethylphosphonate, in parentheses, is used by some marine organisms to insert a C—P bond into their phospholipids. Reaction 2 shows the futile cycle obtained with 2-aminoethylarsonate (59). The symbol -P signifies -P03H2 and its ionized forms, and -P- signifies -P(0)(0H)- and its ionized form (61).

The polymerization reaction of GA was further confirmed by the reaction of ethanolamine with GA observed by light scattering (Figure 4). This amine was highly soluble even after the reaction with GA, and therefore, quite useful for in situ observation and also for the analyses by ESI- MS, which are described later. 

Fig. 21-5, are also used for formation of both phosphatidylcholine and phosphatidylethanolamine. In both cases, the free base, choline, or ethanolamine180a b is phosphorylated with ATP. Choline phosphate formed in this manner is then converted by reaction with CTP to CDP-choline (Eq. 17-58).181 Phosphatidylcholine is formed from this intermediate1813/b while CDP-ethanolamine is used to form phosphatidylethanolamine (Fig. 21-5). These synthetic reactions occur within cell nuclei as well as on surfaces of cytoplasmic membranes.1810...

The reagent is prepared in 67% overall yield from 4,6-diphenyl-2-pyrone by thionation (P4S10) followed by reaction with ethanolamine. 

Scheme I shows the hydrolysis of a phosphate ester in the presence of tris, which can serve as a phosphate acceptor so that O-phosphoryl-tris is a product as well as P(. It has been shown that in the presence of alcohols such as tris and ethanolamine the rate of substrate utilization is increased, that formation of alcohol exceeds that of phosphate, and that the difference is due to the formation of the O-phosphorylamino alcohol (122, 128). The question was Does the reaction with water and with tris emanate from the Michaelis complex or from a phosphoryl enzyme intermediate (E-P) If the reactions with tris and water stem from a phosphoryl enzyme, the ratio of products tris-phosphate and Pi would be independent of the leaving group RO, but if the reactions stem from the reversible complex containing the leaving group, the ratio of products would depend upon the structure of R. It was found that the ratio of free alcohol to phosphate was 2.39 0.02 for nine different substrates, including esters such as p-cresyl phosphate / -naphthyl phosphate, and phosphoenol pyruvate. This experiment established the occurrence of a phosphoryl enzyme intermediate.

Figure 348 Biotinylated liposomes may be formed using biotinylated phosphatidyl ethanolamine. Reaction of NHS-LC-biotin with PE results in amide bond linkages and a long spacer arm terminating in a biotin group.

Esters are prepared by reaction of aldonic acids or lactones with an alcohol in the presence of hydrogen chloride 80 the reaction is slower with 1,4-lactones. Amides are readily formed from lactones by reaction with liquid ammonia followed by evaporation of the solvent.81 D-Gluconamide has also been prepared by treatment of D-glucono-1,5-lactone with concentrated ammonium hydroxide and subsequent precipitation with ethanol.82 A-Substituted aldonamides may be obtained by reaction of the aldono-lactones with ethanolamine, diethanolamine, and related species.83... 

Procedures are reported for the synthesis of ethyleneurea from ethylene glycol or ethanolamine either with urea or with ammonia and carbon dioxide. Pressure and other variables affecting the reactions are discussed and a mechanism is suggested by which amination of the carbon skeleton takes place. 

Ethanolamines are industrially valuable products whose main use is for the manufacture of detergents by reaction with fatty acids. The principal secondary products of ethanolamines are morpholine, ethylenimine and ethylenediamine. 

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