2-[2-(2-hydroxyethylamino)ethylamino]ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.3 g of N,N'-Bis(2-hydroxyethyl)ethylenediamine and 3.0 g of dodecanoyl chloride were reacted together following the procedure under Example 3. This provided 3.3 g of pure product, m.p. 94° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into other 500 ml rounded-flask, were introduced 4.0 g of magnesium oxide and 80 g of distilled water. The mixture was stirred. Thereto was added 7.3 g of N,N'-bis(2-hydroxyethyl)-1,2-diaminoethane prepared above and 250 ml of 1,4-dioxane. 27.5 g of palmitoyl chloride was gradually added dropwise to the resulting mixture for 1 hour under violent stirring at a room temperature. After stirring for 2 hours, the mixture was filtered, and then the filtrate was mixed with 200 ml of chloroform and washed twice with 200 ml of distilled water. Organic phase was cooled to produce solid material, which was recovered by filtration. The solid material was dried and recrystallized from chloroform/acetone and chloroform/hexane, to give 24.3 g of the title compound as white powder, which was identified by IR and NMR. The results are shown in Table 3. under violent stirring at a room temperature After stirring for 2 hours the mixture was filtered the filtrate was mixed with 200 ml of chloroform washed twice with 200 ml of distilled water Organic phase was cooled to produce solid material, which was recovered by filtration The solid material was dried recrystallized from chloroform/acetone and chloroform/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N'-Bis(2-chloroethyl)ethylenediamine (BCE) A solution of N,N'-bis(2-hydroxyethyl)ethylenediamine (5.4 g, 0.036 mol) in SOCl2 (60 mL) was heated at 90° C. for 2 h, then stirred at room temperature for 24 h. Excess SOCl2 was then removed under reduced pressure, and the residue was triturated with isopropanol. Crystallisation from boiling isopropanol (800 mL) containing just enough water to dissolve the solids gave N,N'-bis(2-chloroethyl)ethylenediamine dihydrochloride (BCE.2HCl). Excess SOCl2 was then removed under reduced pressure the residue was triturated with isopropanol Crystallisation containing just enough water to dissolve the solids

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.3 g of N,N'-Bis(2-hydroxyethyl)ethylenediamine and 3.0 g of dodecanoyl chloride were reacted together following the procedure under Example 3. This provided 3.3 g of pure product, m.p. 94° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.3 g of N,N'-Bis(2-hydroxyethyl)ethylenediamine and 3.0 g of dodecanoyl chloride were reacted together following the procedure under Example 3. This provided 3.3 g of pure product, m.p. 94° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N'-Bis(2-chloroethyl)ethylenediamine (BCE) A solution of N,N'-bis(2-hydroxyethyl)ethylenediamine (5.4 g, 0.036 mol) in SOCl2 (60 mL) was heated at 90° C. for 2 h, then stirred at room temperature for 24 h. Excess SOCl2 was then removed under reduced pressure, and the residue was triturated with isopropanol. Crystallisation from boiling isopropanol (800 mL) containing just enough water to dissolve the solids gave N,N'-bis(2-chloroethyl)ethylenediamine dihydrochloride (BCE.2HCl). Excess SOCl2 was then removed under reduced pressure the residue was triturated with isopropanol Crystallisation containing just enough water to dissolve the solids

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N'-Bis(2-chloroethyl)ethylenediamine (BCE) A solution of N,N'-bis(2-hydroxyethyl)ethylenediamine (5.4 g, 0.036 mol) in SOCl2 (60 mL) was heated at 90° C. for 2 h, then stirred at room temperature for 24 h. Excess SOCl2 was then removed under reduced pressure, and the residue was triturated with isopropanol. Crystallisation from boiling isopropanol (800 mL) containing just enough water to dissolve the solids gave N,N'-bis(2-chloroethyl)ethylenediamine dihydrochloride (BCE.2HCl). Excess SOCl2 was then removed under reduced pressure the residue was triturated with isopropanol Crystallisation containing just enough water to dissolve the solids

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N'-Bis(2-chloroethyl)ethylenediamine (BCE) A solution of N,N'-bis(2-hydroxyethyl)ethylenediamine (5.4 g, 0.036 mol) in SOCl2 (60 mL) was heated at 90° C. for 2 h, then stirred at room temperature for 24 h. Excess SOCl2 was then removed under reduced pressure, and the residue was triturated with isopropanol. Crystallisation from boiling isopropanol (800 mL) containing just enough water to dissolve the solids gave N,N'-bis(2-chloroethyl)ethylenediamine dihydrochloride (BCE.2HCl). Excess SOCl2 was then removed under reduced pressure the residue was triturated with isopropanol Crystallisation containing just enough water to dissolve the solids

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N′-bis(2-hydroxyethyl)-ethylenediamine (Aldrich, 14.8 g, 100 mmol) and pyridine (Fluka, 200 mL) was stirred at 0° C. under nitrogen while a solution of toluene-4-sulfonyl chloride (Fluka, 77 g, 400 mmol) dissolved in pyridine (Fluka, 100 mL) was dropped into the solution over a period of 75 minutes. The temperature was slowly raised to room temperature and continued stiffed for 4 hours. Solution was poured into a mixture of ice (250 mL) and hydrochloric acid (concentrated, 250 mL) while stirring to afford a dark sticky oil. Solvents were removed by decantation, product crude washed with water, decanted and re-dissolved in methanol (250 mL). The resulting slurry was isolated by filtration and the crude product was re-dissolved in hot methanol (60° C., 600 mL) and cooled down. Solid product was filtered off and dried in vacuo. Yield 36.36 g (47.5%). Product was verified by NMR. was dropped into the solution over a period of 75 minutes to afford a dark sticky oil Solvents were removed by decantation, product crude washed with water decanted re-dissolved in methanol (250 mL) The resulting slurry was isolated by filtration cooled down Solid product was filtered off dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was prepared by treating N,N′-bis(2-hydroxyethyl)ethylenediamine in methanol with (BOC)2O at room temperature. The reaction mixture was chilled to −15° C. to −20° C. to precipitate the product. After filtration, the precipitate was desiccated to yield the product. The product was prepared The reaction mixture was chilled to −15° C. to −20° C. to precipitate the product After filtration to yield the product

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.0 g of ethyl [3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetate (Example 2) and 1.0 g of bis(2-hydroxyethyl)ethylenediamine are boiled under reflux for 24 h in 8 ml of ethanol. The mixture is cooled, poured onto water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated on a rotary evaporator. The residue is chromatographed on silica gel. After concentration and drying, N-{2-[bis(2-hydroxyethyl)amino]ethyl}-2-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetamide remains as a colorless foam. Rf value: 0.35 (silica gel 60, methylene chloride/methanol=9/1). 1H-NMR (DMSO-d6): 2.5 (m, 6H), 3.1 (m, 2H), 3.4 (m, 4H), 4.2 (bs, 2H), 4.9 (s, 2H), 7.0 (m, 4H), 7.4 (m, 3H), 7.95 (d, 1H), 8.1 (t, 1H), 11.0 ppm (s, 1H). The mixture is cooled poured onto water extracted with ethyl acetate The combined organic phases are dried over sodium sulfate concentrated on a rotary evaporator The residue is chromatographed on silica gel After concentration drying

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into other 500 ml rounded-flask, were introduced 4.0 g of magnesium oxide and 80 g of distilled water. The mixture was stirred. Thereto was added 7.3 g of N,N'-bis(2-hydroxyethyl)-1,2-diaminoethane prepared above and 250 ml of 1,4-dioxane. 27.5 g of palmitoyl chloride was gradually added dropwise to the resulting mixture for 1 hour under violent stirring at a room temperature. After stirring for 2 hours, the mixture was filtered, and then the filtrate was mixed with 200 ml of chloroform and washed twice with 200 ml of distilled water. Organic phase was cooled to produce solid material, which was recovered by filtration. The solid material was dried and recrystallized from chloroform/acetone and chloroform/hexane, to give 24.3 g of the title compound as white powder, which was identified by IR and NMR. The results are shown in Table 3. under violent stirring at a room temperature After stirring for 2 hours the mixture was filtered the filtrate was mixed with 200 ml of chloroform washed twice with 200 ml of distilled water Organic phase was cooled to produce solid material, which was recovered by filtration The solid material was dried recrystallized from chloroform/acetone and chloroform/hexane