2-ethylhexan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.2 parts 30% methanolic Na-methylate solution are added to 64.5 parts 2-ethylhexylamine. 77 parts 2-carbomethoxy-7-oxabicyclo(2,2,1)hept-5-ene are added drop-wise at 30° to 35° C. during cooling. The reaction medium is then stirred for 15 hours and neutralised with 4 parts concentrated hydrochloric acid. 100 parts methylene chloride and 50 parts water are added, the organic phase separated off, and the aqueous phase extracted twice with 25 ml methylene chloride in each instance. The combined organic phases are reduced in a rotary evaporator at a bath temperature of 90° C. and a vacuum of 20 Torr. The residue is heated under a high vacuum to 110° to 120° C. (bath temperature 140° C.). On conclusion of the furane separation, the sedimentation temperature increases and the product distills over. 66.6 parts N(2-ethylhexyl)acrylamide with a boiling point of 123° C. at 0.4 Torr are obtained. during cooling the organic phase separated off the aqueous phase extracted twice with 25 ml methylene chloride in each instance The combined organic phases are reduced in a rotary evaporator at a bath temperature of 90° C. On conclusion of the furane separation the sedimentation temperature increases the product distills over

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 1 liter round-bottom flask equipped with stirrer and Dean Stark trap was charged methyl cyanoacetate (99 grams, 1 mol; obtained from Sigma-Aldrich Co., Milwaukee, Wis.), followed with methanol solvent (150 milliliters), and the mixture was stirred briefly. 2-Ethylhexylamine (130 grams, 1 mol) was slowly added into this mixture, followed with the sequential addition of ethyl acetoacetate (130 grams, 1 mol; obtained from Sigma-Aldrich Co.), and then piperidine (85 grams, 1 mol; obtained from Sigma-Aldrich Co.). The solution was stirred and heated at 100° C. for 12 hours, and then was cooled to room temperature. The mixture was diluted with 2,500 milliliters of methanol and acidified carefully with concentrated hydrochloric acid until a large amount of precipitate had formed. The precipitate was filtered by vacuum and repeatedly washed with deionized water and filtered until the filtrate was of neutral pH. The crude material was recrystallized in warm methanol to afford 170 grams (65 percent yield) of 2-ethylhexyl pyridone as a white solid. Into a 1 liter round-bottom flask equipped with stirrer The solution was stirred was cooled to room temperature had formed The precipitate was filtered by vacuum repeatedly washed with deionized water filtered until the filtrate The crude material was recrystallized in warm methanol

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

Procedure: Similarly to the process reported in example 1, the cyanuryl chloride was reacted with 2-ethyl-1-hexylamine, to obtain the corresponding intermediate 2,4-bischloro-6-(2-ethylhexyl)imino-1,3,5-triazine. Similarly to the process reported in examples 2 and 3, the latter was reacted with two equivalents of p-aminobenzoic acid to give the corresponding diacid, which was then converted to the corresponding diacyl chloride by the action of thionyl chloride.

Conditions: temp:154.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To ethylcyanoacetate (141 g., 1.25 mole) is slowly added 2-ethylhexylamine (129 g., 1.0 mole) over a period of 0.5 hours. The solution is then gradually heated to 154° C. and the ethanol formed is collected over a period of 1.75 hours. The solution is then stripped of all volatiles boiling at or below 88° C./3.0 mm to give N-(2-ethylhexyl)cyanoacetamide, 201.5 g. of 0.5 hours is collected over a period of 1.75 hours below 88° C./3.0 mm

Conditions: temp:154.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To ethylcyanoacetate (141 g., 1.25 mole) is slowly added 2-ethylhexylamine (129 g., 1.0 mole) over a period of 0.5 hours. The solution is then gradually heated to 154° C. and the ethanol formed is collected over a period of 1.75 hours. The solution is then stripped of all volatiles boiling at or below 88° C./3.0 mm to give N-(2-ethylhexyl)cyanoacetamide, 201.5 g. of 0.5 hours is collected over a period of 1.75 hours below 88° C./3.0 mm

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

Procedure: 2-chlorosulphenylbenzoyl chloride (10.35 parts; 0.005M) was slowly added to a stirred solution of 2-ethylhexylamine (29.8 parts; 0.23M;) in diethylether (150 ml) at below 5° C. The reactants were then stirred overnight, allowing the temperature to rise to 18° to 20° C. Iced water was then added and the mix made just acid to Congo red by dropwise addition of of concentrated hydrochloric acid, keeping the temperature below 5° C. The ether layer was then separated and dried over magnesium sulphate. The solution was then filtered and the ether evaporated leaving a syrupy oil. This was boiled with petroleum ether (bp 60°-80° C.), the ether layer decanted from some tarry material and then evaporated to dryness leaving a dark yellow oil. This oil was purified by high vacuum distillation in a Kugelrohr and 8.4 parts pale yellow liquid obtained (Yield 64% theory). to rise to 18° to 20° C was then added the temperature below 5° C The ether layer was then separated dried over magnesium sulphate The solution was then filtered the ether evaporated leaving a syrupy oil the ether layer decanted from some tarry material evaporated to dryness leaving a dark yellow oil This oil was purified by high vacuum distillation in a Kugelrohr and 8.4 parts pale yellow liquid obtained (Yield 64% theory)

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 300 ml reaction vessel equipped with a distillation apparatus, 50 g of 2-ethylhexylamine, 29 g of methyl carbamate and 100 ml of toluene were placed, and to the mixture was added 0.1 g of dibutyl tin oxide as a catalyst and heated with stirring. Methanol formed during the reaction was removed, when the reflux temperature was raised to 110° C., i.e.,the boiling point of toluene, the distillation apparatus was taken off and instead a reflux condenser was attached and the mixture was refluxed by heating for 30 minutes with stirring, then allowed to cool. The toluene was distilled off under reduced pressure, and the residue was washed with n-hexane and collected by filtration to obtain 61 g of N-(2-ethylhexyl)urea. Into a 300 ml reaction vessel heated was removed the mixture was refluxed by heating for 30 minutes with stirring to cool The toluene was distilled off under reduced pressure the residue was washed with n-hexane collected by filtration

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 300 ml reaction vessel equipped with a distillation apparatus, 50 g of 2-ethylhexylamine, 29 g of methyl carbamate and 100 ml of toluene were placed, and to the mixture was added 0.1 g of dibutyl tin oxide as a catalyst and heated with stirring. Methanol formed during the reaction was removed, when the reflux temperature was raised to 110° C., i.e.,the boiling point of toluene, the distillation apparatus was taken off and instead a reflux condenser was attached and the mixture was refluxed by heating for 30 minutes with stirring, then allowed to cool. The toluene was distilled off under reduced pressure, and the residue was washed with n-hexane and collected by filtration to obtain 61 g of N-(2-ethylhexyl)urea. Into a 300 ml reaction vessel heated was removed the mixture was refluxed by heating for 30 minutes with stirring to cool The toluene was distilled off under reduced pressure the residue was washed with n-hexane collected by filtration

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

Procedure: The procedure described in Example 3 is repeated, except that 204 g of allyl-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride and 129 g of 2-ethylhexylamine are used. 17 g of water are split off ayt 115° to 160° C. under 4,000 Pa in the course of 4.5 hours. 292.05 g (92.6% of theory) of a fraction of boiling point 160°-164° C. under 10.7 Pa, nD20 1.5038 and η25 0.68 Pa.s are obtained. 17 g of water are split off ayt 115° to 160° C. under 4,000 Pa in the course of 4.5 hours 292.05 g (92.6% of theory) of a fraction of boiling point 160°-164° C. under 10.7 Pa, nD20 1.5038 and η25 0.68 Pa.s are obtained