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[ CAS No. 106-20-7 ] {[proInfo.proName]}

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Product Details of [ 106-20-7 ]

CAS No. :106-20-7 MDL No. :MFCD00009489
Formula : C16H35N Boiling Point : -
Linear Structure Formula :- InChI Key :SAIKULLUBZKPDA-UHFFFAOYSA-N
M.W : 241.46 Pubchem ID :7791
Synonyms :

Safety of [ 106-20-7 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2922
Hazard Statements:H302-H311-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 106-20-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 106-20-7 ]

[ 106-20-7 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 108-30-5 ]
  • [ 106-20-7 ]
  • [ 68122-19-0 ]
YieldReaction ConditionsOperation in experiment
In toluene at 60℃; Inert atmosphere;
  • 2
  • [ 106-20-7 ]
  • [ 51163-29-2 ]
  • [ 86781-60-4 ]
YieldReaction ConditionsOperation in experiment
72% In hexane Ambient temperature;
  • 3
  • [ 106-20-7 ]
  • [ 201230-82-2 ]
  • [ 558-17-8 ]
  • N,N-di-2-ethylhexylpivalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With 2,2'-azobis(isobutyronitrile); allyltributylstanane; triethylamine In hexane at 80℃; for 8h;
  • 4
  • [ 933-20-0 ]
  • [ 106-20-7 ]
  • [ 154948-55-7 ]
  • 5
  • [ 18933-86-3 ]
  • [ 106-20-7 ]
  • 2,3,4,2',3',4'-hexa-O-benzoyl-6,6'-dideoxy-6,6'-bis[N,N-bis(2-ethylhexyl)amino]-α,α-trehalose [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With sodium iodide In xylene at 150℃; for 16h;
  • 6
  • [ 104-75-6 ]
  • [ 106-20-7 ]
YieldReaction ConditionsOperation in experiment
91% With Co2Rh2/C In toluene at 180℃; for 18h; Autoclave; Inert atmosphere;
Multi-step reaction with 2 steps 1: aq. Na2S2O8, AgNO3, NaOH 2: H2
  • 7
  • [ 106-20-7 ]
  • [ 79-06-1 ]
  • [ 865875-03-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: carbon disulfide; 2-ethyl-N-(2-ethylhexyl)-1-hexanamine at 30℃; for 1.75h; Stage #2: 2-propenamide In water at 30 - 80℃; for 4h; 1 Preparation of di(2-ethylhexyl)dithiocarbamyl propionamide (amide Intermediate) (Compound 1) To a 1-L round bottom flask equipped with an overhead stirrer and a thermocouple was added 280.0 grams (1.16 mol) of di(2-ethylhexyl) amine. 74 mL (1.22 mol) of carbon disulfide was then slowly added over 45 minutes while maintaining a temperature of 30° C. with cooling. The product was post-reacted at 30° C. for 1 hour. Next, 164.8 grams of a 50-weight percent aqueous acrylamide solution (1.16 mol) was added over a 15-minute period and then heated to 80° C. over a 45-minute period. The product was post-reacted at 80° C. for 3 hours. The reactants were cooled to 50° C. and transferred to a 1-L separatory funnel. 300 mL reagent heptanes was added to facilitate separation. The organic layer was transferred to a 1-L flask and volatiles were removed by vacuum distillation. 439.6 grams of a medium yellow, moderate viscosity liquid was recovered.
  • 8
  • [ 106-20-7 ]
  • C69H102N4O7S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: FD&C blue no. 1 With thionyl chloride In chloroform; N,N-dimethyl-formamide at 20 - 60℃; for 4h; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In chloroform; N,N-dimethyl-formamide at 0 - 60℃; for 4h; 1 (Example- 1); A colorant compound having a structure as represented by the above general formula (1) is obtained in a manner as described below. Oynthesis Example (manufacturing a colorant compound as defined by general formula (10) shown below) > EPO ( formula ( IQ ) )5.1 mL of thionyl chloride was dropped into a mixture of 10 g of a colorant compound represented by the above general formula (6), where M is sodium salt, 80 mL of chloroform and 2.4 g of N7N- dimethylformamide, over one hour, at room temperature. After completing the dropping, the temperature of the solution was raised to 600C and stirred for 3 hours at this temperature. Then, a mixture of 15.5 g of di (2-ethylhevxyl) amine and 7.7 g of triethylamine was dropped into the obtained reaction mixture, over one hour at 00C. After completing the dropping, the temperature of the solution was raised to 600C and stirred for 3 hour at this temperature. After the completion of the reaction, the reaction mixture was neutralized by acetic acid and poured into 250 mL- of water. Then, the reaction mixture was subjected to an extraction process by using chloroform and the organic layer was washed with 250 mL of water. After EPO drying the organic layer by means of anhydrous mirabilite, the precipitate was filtered and the solvent in the filtration liquid was distilled off. Then, the distillation residue was refined by means of column chromatography to obtain a compound represented by the formula (10) .The structure of the compound was identified by means iH and i3C NMR analysis, using a nuclear magnetic resonance spectrochemical analyzer (ECA-400: tradename, available from JEOL) , and the purity of the obtained compound was checked by means of HPLC (high performance liquid chromatography, LC2010A: tradename, available from SHIMADZU) . The results of the analysis are shown below. (results of analysis of compound represented by formula (10))(1) Results of iH NMR (400 MHz, CDCl3, room temperature) (FIG. 1) : δ = 0.80 - 0.89 (m, 24H), 1.22 - 1.39 (m, 42H), 2.81 - 3.00 (m, 8H), 3.60 - 3-.70 (m, 4H), 4.75 - 4.85 (m,4H), 6.77 - 6.79 (m, 4H), 6.95 (dd, IH),.7.32 (d, IH), 7.38 (m, 2H), 7.49 - 7.57 (m, 7H), 7.62 (br, 2H), 7.69 - 7.75 (m, 2H), 8.31 (d, IH)(2) Results of 13C NMR (100 MHz, CDCl3, room temperature) : δ = 10.1, 12.5, 14.0, 23.0, 23.4, 28.6, 30.3, 37.7, 46.6, 53.4, 113.2, 125.2, 126.6, 126.8, 128.0, 128.7, EPO 129.1, 130.0, 130.1, 130.3, 130.4, 136.2, 137.0, 140.4, 141.7, 147.4, 156.1, 182.1(3) Results of HPLC: purity =• 96.7 area%, retention time.: 9.3 minutes (MeOH/H2O = 95/5)
  • 9
  • vanadium (IV) oxide sulfate * 5 water [ No CAS ]
  • [ 106-20-7 ]
  • vanadium(IV) oxide bis(di-2-ethylhexyldithiocarbamate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With carbon disulfide; sodium hydroxide In methanol; acetone 1 Vanadium(IV) oxide bis(di-2-ethylhexyldithiocarbamate) STR5 Molecular weight: 700.103 64 g of a 50% strength sodium hydroxide solution are added to 400 ml of methanol. 192.8 g of di-2-ethylhexylamine are added to this mixture. 50 ml of carbon disulfide are added dropwise over a period of 20 minutes, with mechanical stirring, using a low-temperature condenser. The mixture is stirred for a further 3 hours. A solution of 100 g of vanadium(IV) oxide sulfate pentahydrate in 250 ml of methanol is then added dropwise over a period of one hour. The mixture is left to stand overnight. The solvent is then evaporated off under vacuum and the residue is taken up in acetone. The sodium sulfate which has precipitated out is filtered off and the acetone is distilled off. A viscous brown-black oil was obtained. Yield: 85% of theory, 235.5 g Purity: by nitrogen determination--94.97%
  • 10
  • [ 94266-20-3 ]
  • [ 106-20-7 ]
  • [ 106-89-8 ]
  • [ 96-24-2 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide In CS2; aqueous HClO4 I.c (c) (c) Method C The same procedure of Method B was followed, except that 3-chloro-1,2-propanediol was prepared in situ from epichlorohydrin as follows. Epichlorohydrin (46.25 grams) was suspended in 1M aqueous HClO4 (50 ml). The suspension was stirred at room temperature until the solution turned clear (about 1.5 hours). The clear aqueous solution was further heated at 50° C. for another half hour. After cooling to room temperature, the aqueous solution was allowed to react with the aqueous solution of sodium bis(2-ethylhexyl)dithiocarbamate derived from bis(2-ethylhexyl)amine (120.8 grams), CS2, (33 ml) and 2M aqueous NaOH (12.5 ml). The product, having an identical C-13 NMR spectrum as that of product prepared in Method A, was obtained in a 95% yield (185.7 grams).
  • 11
  • [ 139508-81-9 ]
  • [ 106-20-7 ]
  • 1-Isobutyl-2,8-bis[di(2-ethylhexyl)amino]-3,7,9-trioxa-1-aza-2,8-diphosphaspiro[4.5]decane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In toluene 20 1-Isobutyl-2,8-bis[di(2-ethylhexyl)amino]-3,7,9-trioxa-1-aza-2,8-diphosphaspiro[4.5]decane EXAMPLE 20 1-Isobutyl-2,8-bis[di(2-ethylhexyl)amino]-3,7,9-trioxa-1-aza-2,8-diphosphaspiro[4.5]decane The procedure of Example 10 is repeated using 5.0 g (16.4 mmol) of 1-isobutyl-2,8-dichloro-3,7,9-trioxa-1-aza-2,8-diphosphaspiro[4.5]decane, the compound of Example 8, 7.9 g (32.8 mmol) of di-2-ethylhexylamine and 4.6 mL (32.8 mmol) of triethylamine in 120 mL of toluene. The title compound is isolated in a yield of 10.2 g as an oil and is identified by mass spectrometry: m/z=715.
  • 12
  • [ 288-32-4 ]
  • [ 106-20-7 ]
  • [ 106-89-8 ]
  • di-2-ethylhexyl-(3-imidazolyl-2-hydroxypropyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In 2-methyl-propan-1-ol; water 4.a Di-2-ethylhexyl-(3-imidazolyl-2-hydroxypropyl)-amine (a) 241.5 g of di-2-ethylhexylamine (1 mole) are run into 92.5 g of epichlorohydrin (1 mole) and 10 ml of water at 35° C., in a 1 liter stirred flask equipped with a dropping funnel, stirrer, thermometer and reflux condenser, and the mixture is then kept at this temperature for 22 hours. At that point, there is no longer any free epichlorohydrin in the reaction mixture. 68.1 g of imidazole (1 mole) in 400 ml of isobutanol are then run in, the mixture is heated to 100° C., and 140 g of 50% strength potassium hydroxide solution (1.25 moles) are added dropwise in the course of two hours. After 3 hours, 1.13 milliequivalents of chloride/g are detectable in the batch. The batch is cooled and is repeatedly washed with water, using a total of 1.5 liters of the latter. After concentrating the organic phase under reduced pressure, 273 g of di-2-ethylhexyl-(3-imidazolyl-2-hydroxypropyl)-amine remain.
  • 13
  • 3,3,3-Trifluoropropyl(bis(2-ethylhexyl)aminodimethoxysilane - A [ No CAS ]
  • [ 106-20-7 ]
  • [ 429-60-7 ]
  • [ 1068-55-9 ]
  • [ 227768-97-0 ]
YieldReaction ConditionsOperation in experiment
98% In tetrahydrofuran IX Example IX Example IX 3,3,3-Trifluoropropyl(bis(2-ethylhexyl)aminodimethoxysilane - A 500 mL round bottomed flask was charged with tetrahydrofuran (300 mL) and isopropylmagnesium chloride (25 nil of a 2.0 M solution in THF, 50 mmol). The contents were cooled to 15°C. Bis(2-ethylhexyl)amine (50 mmol) was added over fifteen minutes via pressure equalizing addition funnel. The cold bath was removed and the contents stirred for two hours. 3,3,3-Trifluoropropyltrimethoxysilane (45 mmol) was added via pressure equalizing addition funnel. The contents were brought to reflux (65-70°C) for two hours, and reaction progress was monitored by GC. Isolation was accomplished by removing the THF via rotary evaporation, taking the residue up in ether (250 mL), filtration and ether removal via rotary evaporation. Purification was accomplished by distillation to provide 3,3,3-trifluoropropyl bis(2-ethylhexyl)aminodimethoxysilane (44 mmol; 98% yield). C21H44NO2SiF3(mw = 427.66) bp = 200°C at 1.4 mmHg; 1H NMR: (CDCl3) δ 3.5 (s, 6H), 2.6-2.4 (dd, 4H), 2.2-2.0 (m, 2H), 1.6-1.1 (m, 18H), 1.0-0.7 (m, 14H); 13C NMR: (CDCl3) δ 128 (quartet, J = 275 Hz), 50.4, 48.5, 39.4, 36.9, 30.8, 29.1, 28.2 (quartet, J = 30 Hz), 23.2, 14.2, 10.3, 3.2; MS: m/z (relative abundance) 328 (100), 230 (25.6), 155 (7.4), 109 (2.9).
  • 14
  • [ 106-20-7 ]
  • [ 3643-70-7 ]
  • 3,9-bis[di(2-ethylhexyl)amino]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine In toluene 1 Example 1 Example 1 3,9-Bis(di-2-ethylhexylamino)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]undecane A flame-dried, 500 ml, 4 necked flask equipped with an overhead stirrer, thermometer, addition funnel and reflux condenser is charged with 10.7 g (40 mmol) of 3,9-di-chloro-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]undecane and 250 ml of dry toluene under a dry nitrogen atmosphere. A mixture of 19.3 g (80 mmol) of di-2-ethylhexylamine and 8.1 g (80 mmol) of triethylamine at 0°C is added dropwise to the stirred contents of the flask while the temperature is maintained below 5°C with ice cooling. When the addition is complete, the mixture is warmed to ambient temperature and continually stirred until a filtered aliquot gives a negative Beilstein test (approximately 4 hours). The reaction mixture is then filtered to remove triethylamine hydrochloride and the filter cake is washed with two 25 ml portions of dry toluene. The combined filtrates are concentrated in vacuo to remove all volatiles to give 26.0 grams (96% yield) of the title compound as a colorless oil. Analysis: Calcd. forC37H76N2O4P2: C, 65.8 %; H, 11.3 %; N, 4.1 %. Found: C, 65.7 %; H, 11.7 %; N, 4.1 %.
  • 15
  • [ 106-20-7 ]
  • [ 504-02-9 ]
  • [ 941572-81-2 ]
YieldReaction ConditionsOperation in experiment
74% In toluene at 0 - 180℃; for 4h; 1.1 9.25 g (0.08 mole) of cyclohexane-1.3-dion were dissolved in 30 ml. toluene. The mixture was cooled down to 0°C and then 19.71 g (0.08 mole) of bis-2-ethylhexylamine were added under stirring. The mixture was heated at 180 °C for 4 hours in an autoclave. After distilling off the solvent and unreacted amine at 150 °C under 1x10"3 mbar pressure N,N-bis-2-ethyl- hexylamino-cyclohexene-3-one is obtained as a darkbrownish oil in yields of 74 %. b.p. = 1800C (0.1 mbar).
  • 16
  • [ 17228-64-7 ]
  • [ 106-20-7 ]
  • [ 1033752-61-2 ]
YieldReaction ConditionsOperation in experiment
75% With [(1,3-(2,6-diisopropylphenyl)imidazol-2-ylidene)(3-chloropyridyl)palladium(II) dichloride]; potassium <i>tert</i>-butylate In 1,2-dimethoxyethane at 50℃; Inert atmosphere;
  • 17
  • [ 106-20-7 ]
  • [ 32276-56-5 ]
  • [ 220324-36-7 ]
YieldReaction ConditionsOperation in experiment
60% With triethylamine In tetrahydrofuran at 20℃;
  • 18
  • [ 106-20-7 ]
  • [ 1710-98-1 ]
  • [ 1202254-31-6 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine In tetrahydrofuran at 20℃;
  • 19
  • [ 123-05-7 ]
  • [ 106-20-7 ]
  • [ 104-76-7 ]
  • [ 1860-26-0 ]
YieldReaction ConditionsOperation in experiment
1: 86.2 %Chromat. 2: 8.7 %Chromat. With hydrogen at 80℃; for 52h; Autoclave; Inert atmosphere; Industry scale; Industrial Synthesis of tris(2-ethylhexyl)amine(tris-EH) The experiment was carried out in a stirring autoclave. 4000 kg of bis(2-ethylhexylamine (di-EH) was placed in the reactor in which from 40 to 150 kg of the carbon-supported, palladium-comprising suspended catalyst comprising 5% of Pd on carbon (water content: about 50%) had been installed. The reactor was flushed with nitrogen. A low hydrogen pressure was set and the mixture was subsequently heated to the reaction temperature. As soon as the reaction temperature had been reached, the hydrogen pressure was increased to the desired reaction pressure. The aldehyde 2-ethylhexanal (2-EH, from 2120 to 2320 kg) was subsequently added continuously. The di-EH conversion was determined during the course of the experiment and the aldehyde was added in such an amount that a conversion of at least 95% was achieved. This resulted in molar aldehyde excesses of from 0.1 to 9%. The predominant by-product formed was small amounts of ethylhexanol (E-ol). Table 3 shows the results of the 33 reaction batches (reaction parameters and composition of the organic phase in GC-% by area). After the 1st, 3rd, 8th and 15th batches, fresh catalyst was introduced into the reactor, as a result of which the amount of catalyst increased to a final value of 150 kg. From batch 16, the catalyst was recirculated 17 times without an appreciable decrease in the catalyst activity.
  • 20
  • [ 123-05-7 ]
  • [ 106-20-7 ]
  • [ 1860-26-0 ]
YieldReaction ConditionsOperation in experiment
96.0 %Chromat. With hydrogen at 140℃; for 14h; Autoclave; Inert atmosphere; Industry scale; Industrial Synthesis of tris(2-ethylhexyl)amine(tris-EH) The experiment was carried out in a stirring autoclave. 4000 kg of bis(2-ethylhexylamine (di-EH) was placed in the reactor in which from 40 to 150 kg of the carbon-supported, palladium-comprising suspended catalyst comprising 5% of Pd on carbon (water content: about 50%) had been installed. The reactor was flushed with nitrogen. A low hydrogen pressure was set and the mixture was subsequently heated to the reaction temperature. As soon as the reaction temperature had been reached, the hydrogen pressure was increased to the desired reaction pressure. The aldehyde 2-ethylhexanal (2-EH, from 2120 to 2320 kg) was subsequently added continuously. The di-EH conversion was determined during the course of the experiment and the aldehyde was added in such an amount that a conversion of at least 95% was achieved. This resulted in molar aldehyde excesses of from 0.1 to 9%. The predominant by-product formed was small amounts of ethylhexanol (E-ol). Table 3 shows the results of the 33 reaction batches (reaction parameters and composition of the organic phase in GC-% by area). After the 1st, 3rd, 8th and 15th batches, fresh catalyst was introduced into the reactor, as a result of which the amount of catalyst increased to a final value of 150 kg. From batch 16, the catalyst was recirculated 17 times without an appreciable decrease in the catalyst activity.
  • 21
  • [ 106-44-5 ]
  • [ 106-20-7 ]
  • [ 7693-46-1 ]
  • [ 1182705-76-5 ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: p-cresol; 4-Nitrophenyl chloroformate With triethylamine In dichloromethane at 20℃; for 96h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In dichloromethane at 20℃; for 120h; Inert atmosphere;
  • 22
  • [ 106-20-7 ]
  • [ 103-16-2 ]
  • [ 7693-46-1 ]
  • [ 1285718-51-5 ]
YieldReaction ConditionsOperation in experiment
27% Stage #1: 4-Benzyloxyphenol; 4-Nitrophenyl chloroformate With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In dichloromethane at 20℃; Inert atmosphere;
  • 23
  • [ 106-20-7 ]
  • [ 620-92-8 ]
  • [ 7693-46-1 ]
  • [ 1182705-78-7 ]
YieldReaction ConditionsOperation in experiment
76.8% Stage #1: bis-(4-hydroxyphenyl)methane; 4-Nitrophenyl chloroformate With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In dichloromethane at 20℃; Inert atmosphere;
  • 24
  • [ 106-20-7 ]
  • [ 10439-48-2 ]
  • [ 7693-46-1 ]
  • [ 1285718-53-7 ]
YieldReaction ConditionsOperation in experiment
35% Stage #1: 4,4'-propanediyldioxy-di-phenol; 4-Nitrophenyl chloroformate With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In dichloromethane at 20℃; Inert atmosphere;
  • 25
  • [ 106-20-7 ]
  • [ 70856-53-0 ]
  • [ 7693-46-1 ]
  • [ 1285718-54-8 ]
YieldReaction ConditionsOperation in experiment
32.1% Stage #1: α-(Hydrogen)-ω-(hydroxy)-(oxy-1,4-phenyleneoxy-1,10-decamethyleneoxy-1,4-phenylene); 4-Nitrophenyl chloroformate With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In dichloromethane at 20℃; Inert atmosphere;
  • 26
  • [ 106-20-7 ]
  • [ 44995-78-0 ]
  • [ 1332305-90-4 ]
YieldReaction ConditionsOperation in experiment
62% With triethylamine In tetrahydrofuran at 20℃;
  • 27
  • [ 106-20-7 ]
  • [ 618-88-2 ]
  • [ 1360595-64-7 ]
YieldReaction ConditionsOperation in experiment
83.4% Stage #1: 5-nitrobenzene-1,3-dicarboxylic acid With thionyl chloride In chloroform at 10 - 65℃; for 3h; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In chloroform at 64℃; for 3h; 1 Example 1; [0109]Azo compounds represented by the formula (1) wereobtained in the following way.[0110] Synthesis Example 1[0111] Synthesis of compound (38):A compound (38) in which, in the formula (1), Ri to R4, R6 , R7 , R9 , R11 , R13 and R15 are hydrogen atoms, Ri2 and Ri4 are L2R21R22 groups, where L2 is a carboxylic acid tertiary amide group and R2i and R22 are 2-ethylhexyl groups, R5 and R8 are COORi7 groups, and Ri0 , R16 and R17 are methyl groups was synthesized according to the following synthesis scheme. [0112] First, a compound (54) was synthesized by using compounds (52) and (53). To 50.00 parts of chloroform, 5.00 parts of the compound (52) was added, and these were ice-cooled to 10°C or below, where 11.00 parts of thionyl chloride was added thereto. Thereafter, the mixture obtained was stirred at 65°C for 3 hours. This was again ice-cooled to 10°C or below, and then 11.70 parts of the compound (53) and 6.00 parts oftriethylamine were added thereto. Thereafter, the mixture obtained was stirred at 65°C for 3 hours.After the reaction was completed, the reaction product obtained was extracted with chloroform, and thenpurified by column chromatography (eluting solution:ethyl acetate/heptane) to obtain 13.00 parts of the compound (54) as an intermediate (yield: 83.4%).
  • 28
  • [ 106-20-7 ]
  • Zinc Di-2-ethylhexyldithiocarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With carbon disulfide; zinc oxide C.6.C Preparation of Zinc Di-2-ethylhexyldithiocarbamate (FC-577-239) Comparative Example 6C Preparation of Zinc Di-2-ethylhexyldithiocarbamate (FC-577-239) To a 250 mL round bottomed flask was placed 48.30 g of di-2-ethylhexylamine and 8.10 g of zinc oxide. Carbon disulfide, 16.0 g, was then added dropwise, and the mixture was stirred for 30 minutes. The flask was then stirred and heated for 2 hours at 70° C., and then stirred for an addition 2 hours at 90° C. A vacuum was then applied to remove water of reaction and the temperature was increased to 130° C., and the reaction was maintained in this state for 3 hours. The pale yellow material was then filtered through Celite at 120° C., to give, upon a pale yellow liquid with a Zn content of 8.1%.
  • 29
  • [ 50-00-0 ]
  • [ 106-20-7 ]
  • [ 90726-43-5 ]
  • [ 1414376-28-5 ]
YieldReaction ConditionsOperation in experiment
57% In methanol at 0 - 40℃; for 144h;
  • 30
  • [ 106-20-7 ]
  • [ 68-11-1 ]
  • bis(2-ethylhexylammonium)thioglycolate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In neat (no solvent) at 20℃;
  • 31
  • [ 75-15-0 ]
  • [ 106-20-7 ]
  • [ 77414-73-4 ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 1h; Cooling with ice;
In ethanol at 5℃; Preparation of [Ni(behdtc)2] A mixture of bis(2-ethylhexyl)amine (10 mmol, 2.9 mL) and carbondisulfide(10mmol,0.6mL)inethanolwerekeptice-cold(5°C) to form a yellow solution of the dithiocarbamic acid.
  • 32
  • [ 4480-83-5 ]
  • [ 106-20-7 ]
  • [ 1338217-74-5 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran at 20℃; for 2h; 1 A mixed solution of 27 g (0.20 mole) of diglycolic acid and 130 g (1.27 moles) of acetic anhydride was heated under reflux for 4 hours. Thereafter, the excess acetic anhydride and acetic acid formed by reaction were distilled off in vacuum. To the concentrate (reaction intermediate), 150 g of tetrahydrofuran was added, and then 48 g (0.20 mole) of di(2-ethylhexyl)amine was added dropwise. Stirring was continued for 2 hours at room temperature, followed by vacuum concentration to remove the reaction solvent, tetrahydrofuran, yielding 70 g of the reaction product as a pale yellow liquid (Example 1). The reaction scheme is as shown below.
  • 33
  • [ 106-20-7 ]
  • [ 1357467-59-4 ]
  • [Ag{di(2-EtHex)Am}2][Tf2N] [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In dichloromethane at 20℃; for 1h;
  • 34
  • [ 106-20-7 ]
  • [ 552-16-9 ]
  • [ 1208124-66-6 ]
  • C31H45N5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: ortho-nitrobenzoic acid With thionyl chloride In chloroform at 60℃; for 1h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In chloroform at 10 - 80℃; for 2h; Stage #3: 3-cyano-4-methyl-6-oxo-2-pyridone With hydrogenchloride; sodium sulfide; sodium nitrite In methanol; ethanol; water at 10 - 75℃; for 2h; 1 Production Example 1: production of compound 5 [0069] In a nitrogen atmosphere, 29 parts of thionyl chloride were added dropwise to 10 parts of o-nitrobenzoic acid in 100 parts of chloroform and further reacted at 60°C for 1 hour. After the completion of reaction, the mixture was cooled to 10°C or lower, and 9 parts of triethylamine and 15 parts of di ( 2-ethylhexyl ) amine were added dropwise thereto in this order. The mixture was further stirred at 80°C for 2 hours. After the completion of reaction, extraction with chloroform was performed. The extract was concentrated under reduced pressure to obtain 18 parts of an intermediate (5-1) . [0070] 50 parts of ethanol and 18 parts of a 20% aqueous sodium sulfide solution were added to 10 parts of the intermediate (5-1) and reacted at 75°C for 1 hour. After the completion of reaction, extraction with chloroform was performed, and the resulting solution was concentrated under reduced pressure to obtain 7.4 parts of an intermediate (5-2) . [0071] 3.4 parts of concentrated hydrochloric acid and 59 parts of methanol were added to 5.9 parts of the intermediate (5-2), and the mixture was cooled to 10°C or lower. To this solution, a solution of 1.4 parts of sodium nitrite in water (2.0 parts) was slowly added dropwise so as not to become 10 °C or higher, and the mixture was further reacted for 1 hour. Subsequently, 0.5 parts of sulfamic acid were added thereto, and the mixture was stirred for 20 minutes to obtain a diazonium salt solution. [0072]Next, a solution of 2.7 parts of 3-cyano-4-methyl-6- oxo-2-pyridone in 25 parts of N, N-dimethylformamide and 20 parts of methanol was cooled to 10°C or lower, and the diazonium salt solution was added dropwise thereto with the temperature kept at 10 °C or lower. The pH of . the reaction solution was adjusted to 5 to 6 by the addition of a saturated aqueous solution of sodium carbonate, and the resulting solution was reacted at 10°C or lower for 2 hours. After the completion of reaction, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 5.2 parts of a compound (5). [0073] The obtained compound (5) was tested for its purity using high-performance liquid chromatography (HPLC) (LC2010A, manufactured by Shimadzu Corp. ) . In addition, the compound (5) was structurally determined using a time-of-flight mass spectrometer (TOF-MS) (LC/MSD TOF, manufactured by Agilent Technologies, Inc.) and a nuclear magnetic resonance spectrometer (NMR) (ECA-400, manufactured by JEOL Ltd. ) . [0074] Results of analyzing compound (5) (Eluent: CH3OH:H20 = 90: 10, flow rate: 1.0 ml/min, detection wavelength: 254 nm) retention time: 9.6 minutes, purity: 99.5 area% [0075] m/z=522.3458 (M+H ) " NMR (400 MHz, CDC13, room temperature) results (see FIG. 1)> δ [ppm] = 8.59 (1H, s), 7.87 (1H, d) , 7.54-7.49 (1H, m) , 7.30 (2H, m) , 3.52 (2H, s) , 3.25 (2H, d) , 2.64 (3H, s), 1.86-1.82 (1H, m) , 1.51-0.63 (30H, m)
  • 35
  • [ 106-20-7 ]
  • [ 556-52-5 ]
  • C19H41NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 110℃; for 3h; Inert atmosphere; Intermediate 4 Bis(2-ethylhexyl)amine (2010.0 g) was heated to 110° C. under a nitrogen atmosphere in a round bottom flask equipped with a condenser, addition funnel, and mechanical stirrer. Glycidol (685 g) was added dropwise to the reactor over 2 h with vigorous stirring. After completing the glycidol addition, stirring was continued for 1 h. The product was purified via vacuum distillation (165-175° C.; 1.0 mm Hg).
at 110℃; for 3h; Inert atmosphere; Large scale; 2 Bis (2- ethylhexyl) amine (2010.0 g) was heated to 110 °C under a nitrogen atmosphere in a round bottom flaskequipped with a condenser, addition funnel, and mechanical stirrer. Glycidol (685 g) was added dropwise to the reactorover 2 h with vigorous stirring. After completing the glycidol addition, stirring was continued for 1 h. The product was purified via vacuum distillation (165- 175 °C; 1.0 mm Hg) .
at 110℃; for 3h; Inert atmosphere; 4 Bis(2-ethylhexyl)amine (2010.0 g) was heated to 110 °C under a nitrogen atmosphere in a round bottom flaskequipped with a condenser, addition funnel, and mechanical stirrer. Glycidol (685 g) was added dropwise to the reactorover 2 h with vigorous stirring. After completing the glycidol addition, stirring was continued for 1 h. The product waspurified via vacuum distillation (165- 175 °C; 1.0 mm Hg) .
  • 36
  • [ 106-20-7 ]
  • [ 77-78-1 ]
  • [ 1501942-51-3 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In acetonitrile for 48h; Reflux;
  • 37
  • [ 106-20-7 ]
  • [ 1663-67-8 ]
  • [ 823807-37-0 ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine In chloroform for 24h; Reflux;
  • 38
  • [ 627-63-4 ]
  • [ 106-20-7 ]
  • C36H70N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine In chloroform at 0℃; for 2h; Inert atmosphere;
  • 39
  • [ 106-20-7 ]
  • [ 79-04-9 ]
  • 2-chloro-N,N-di(2-ethylhexyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In dichloromethane for 2h;
90% With triethylamine In chloroform [10054] D2EHAG was synthesized as follows First, as shown in the following reaction formula (II), 23.1 g (0.1 mol) of commercially available di(2-ethylhexyl)amine and 10.1 g (0.1 mol) of triethylamine were taken and chloroform was added thereto and dissolved. Next, 13.5 g (0.12 mol) of 2-chloroacetyl chloride was added dropwise thereto and the obtained mixture was washed once with 1 mol/l hydrochlonc acid and then washed with ion exchanged water, and the chloroform phase was separated.10055] Next, anhydrous sodium sulfate was added thereto in an appropriate amount (approximately 10 to 20 g) for dehydration, followed by filtration to obtain 29.1 g of yellow liquid. The structure of this yellow liquid (reaction product) was identified using a nuclear magnetic resonance analyzer (NMR) and the above yellow liquid was confirmed to have the structure of 2-chloro-N,N-di(2-ethylhexyl)acetamide (hereinafier, referred to as “CDEHAA”). It is noted that the yield of CDEHAA was 90% with respect to di(2-ethylhexyl) amine, which is a raw material.
85% With triethylamine In chloroform at 20℃; for 3h; Cooling with ice; II Synthesis of D2EHAG The synthesis of D2EHAG was carried out in the following way. First, as shown in the following reaction formula (II), 2.41 g of commercially available di(2-ethylhexyl)amine (0.1 mol) and 1.01 g of triethyl amine (0.1 mol) were isolated, dissolved by adding chloroform to this, then in succession stirred while maintaining at a temperature in an ice bath, and 13.5 g of 2-chloroacetyl chloride (0.12 mol) was slowly added by dropping. After adding by dropping completed, it was stirred for 3 hours at room temperature. After stirring completed, it was washed once with 1 mol/L hydrochloric acid, subsequently washed several times with ion exchange water, and then the chloroform phase was isolated. [0038] Next, anhydrous sodium sulfate was added in the appropriate amount (about 10 to 20 g), and after evaporating, was filtered under reduced pressure, and the solvent was distilled in an evaporator, thereby obtaining 29.1 g of yellow liquid. The structure of this yellow liquid (reaction product) was identified using a nuclear magnetic resonance instrument (NMR), upon which the above-mentioned yellow liquid was confirmed as being 2-chloro-N,N-di(2-ethylhexyl)acetamide (hereinafter referred to as “CDEHAA”). It should be noted that the yield of CDEHAA was 85% relative to di(2-ethylhexyl)amine, which was the source material.
With triethylamine In dichloromethane at 20℃; for 3h;
Stage #1: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In chloroform for 4h; Cooling with ice; Stage #2: chloroacetyl chloride In chloroform at 20℃; for 19h; 1 0.16 mol of Di(2-ethylhexyl)amine (38.6 g) and 0.16 mol (16.2 g) triethylamine of were mixed in chloroform, and it agitated in the ice bath for about 4 hours. 0.18 mol (19.9 g) chloroacetyl chloride of was dropped at this mixed solution in the ice bath. It agitated at the room temperature after dropping for further 19 hours. The obtained chloroform fluid was sufficiently washed with distilled water after the reaction stop. Decompression distilling off of the chloroform was carried out for this chloroform fluid after drying with sodium sulfate and the 2-chloro-N,N-di(2-ethylhexyl) acetamide (CDEHAA) was obtained.
With TEA In dichloromethane at 20℃; for 3h;
24.26 g With anhydrous sodium carbonate In water monomer at 20 - 28℃; for 7h; 1.1; 2-7 The preparation method of the amide derivative of the present embodiment comprises the following steps: 1) Add sodium carbonate in a 100mL four-necked flask, add water and stir to dissolve, then add 19.33g (0.08mol) of diisooctylamine, stir, add 11.75g of chloroacetyl chloride dropwise at room temperature, add dropwise in 1 hour, then control The temperature was reacted at 28° C. for 6 hours, then the reaction was terminated, the aqueous phase was separated, and 40 mL of 10wt% hydrochloric acid was added to the organic phase to carry out acidification and water washing, and after the water was separated, a small amount of water and low-boiling substances were distilled to obtain product A;

  • 40
  • [ 106-20-7 ]
  • [ 79-04-9 ]
  • 2-chloro-N,N-diethylhexylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane I.A Step A: Step A: Synthesis of 2-chloro-N,N-diethylhexylacetamide To a three-necked flask under agitation and under nitrogen are added 7.46 mL (2 eq.) of bis(2-ethylhexyl)-amine, 50 mL of dichloromethane and 3.5 mL (2 eq.) of triethylamine that are cooled to -30° C. with a dry ice/acetone bath. 2 mL (1 eq.) of chloroacetyl chloride are added dropwise and the reaction medium is left for 3 hours at ambient temperature. After this time, it is poured onto 50 mL of distilled water, decanted and the aqueous phase extracted with 50 mL of dichloromethane. The dichloromethane phases are washed with 50 mL of distilled water, dried over magnesium sulphate, filtered and evaporated to dryness in a rotary evaporator. The 7.26 g of yellow oil thus obtained are subjected to silica gel column chromatography (80 g-63-200 μm particle size) using a dichloromethane/methanol mixture 98:2 v/v as eluent.
  • 41
  • [ 106-20-7 ]
  • C24H43NO4 [ No CAS ]
  • N,N,N′,N′-tetrakis(2-ethylhexyl)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;
  • 42
  • [ 106-20-7 ]
  • N,N,N′,N′-tetraoctyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxamides [ No CAS ]
  • N,N,N′,N′-tetraoctyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxamides [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;
  • 43
  • [ 106-20-7 ]
  • N,N,N′,N′-Tetrabutyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxamides [ No CAS ]
  • N,N,N′,N′-Tetrabutyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxamides [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;
  • 44
  • [ 106-20-7 ]
  • exo-3,6-epoxy-hexahydrophthalic anhydride [ No CAS ]
  • C24H43NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With dmap In dichloromethane at 20℃; for 0.5h;
  • 45
  • [ 5781-53-3 ]
  • [ 106-20-7 ]
  • methyl di-(2-ethylhexyl)oxamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine In diethyl ether at -10 - 20℃; for 1h; 7 Synthesis of methyl di-2-ethylhexylamino oxamate Di-2-ethylhexyl amine (33.63 g, 139.3 mmol, 1.00 eq) and NEt3 (27.76 g, 274.4 mmol, 1.97 eq) were dissolvedin diethyl ether (120 mL) at -10 °C. Monomethyl oxalyl chloride (17.87 g, 145.9 mmol, 1.05 eq), dissolved in diethyl ether(180 mL), was added slowly. The reaction mixture was stirred for another hour at room temperature, the formed precipitatewas filtered off and the resulting crude product was washed with water and concentrated in vacuo. The product wasisolated as yellowish pale oil (40.14 g, 122.6 mmol, 88%) upon distillation (110 °C, 3*10-2 mbar).1 H-NMR (300 MHz, MeCN-d3): δ / ppm = 3.80 (s, 3H, COOCH3), 3.38 - 3.17, 3.15 - 3.05 (m, 4H,CONCH2CH(CH2CH3)(CH2)3CH3), 1.79 - 1.54 (m, 2H, CONCH2CH(CH2CH3)-(CH2)3CH3), 1.41 - 1.13 (m, 16H,CONCH2CH(CH2CH3)(CH2)3CH3), 0.98 - 0.79 (m, 12H, CONCH2CH(CH2CH3)(CH2)3CH3).13C-NMR (75 MHz, MeCN-d3): δ / ppm = 165.1 (COOCH3), 163.6 (CON), 52.9 (COOCH3), 51.8, 47.1(CONCH2CH(CH2CH3)(CH2)3CH3), 38.0, 37.2 (CONCH2CH(CH2CH3)-(CH2)3CH3), 31.1, 31.0(CONCH2CH(CH2CH3)(CH2)3CH3), 29.4, 29.3 (CONCH2CH-(CH2CH3)CH2(CH2)2CH3), 24.5, 24.3(CONCH2CH(CH2CH3)CH2CH2CH2CH3), 23.7, 23.7 (CONCH2CH(CH2CH3)(CH2)2CH2CH3), 14.4, 14.3(CONCH2CH(CH2CH3)(CH2)3CH3), 11.1, 11.0, 10.9, 10.9 (CONCH2CH(CH2CH3)(CH2)3CH3).ESI-MS (MeOH): pos.: m/z (%) = 350.1 (7) [C19H37NO3Na]+.HR-MS (MeOH): pos.: m/z = gef. 350.2665, ber. 350.2666 [C19H37NO3Na]+.
  • 47
  • [ 106-20-7 ]
  • [ 21062-20-4 ]
  • 2,2’-oxybis(N-(2-ethylhexyl)acetamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium hydroxide In diethyl ether; water at 20℃; for 15h; General Procedure 1: Synthesis of Diglycolamides by Schotten-Baumann Reaction General procedure: Diglycolyl chloride (0.85 g, 5 mmol) in Et2O (30 mL) was added dropwise to a solution of amine (30 mmol) and NaOH (1.2 g, 30mmol) in water (36 mL) at 0 °C over 30 min. The mixture was stirred at 0 °C for 2 h, and then the phases were separated. The aqueous layer was saturated with NaCl and extracted with Et2O (3 × 30 mL). An aqueous solution of 10 % HCl (20 mL) was added to the combined organic layers. The mixture was shaken vigorously to facilitate formation of clumps of ammonium salts, floating between the two phases. The organic layer was washed two more times with HCl solution (20 mL) and then filtered through a glass frit (G3). A poly(4-styrenesulfonic acid) solution (4 wt%, 25 mL) in water was added to the organic layer. The mixture was shaken vigorously to facilitate formation of polymeric salts as an amorphous material floating between the layers. The organic layer was washed with water and then separated from the polymeric salt. It was dried with MgSO4, where upon the solvent was removed by vacuum evaporation to afford the DGAs, which had a purity of ≥97 % according to the 1H NMR spectra.
  • 48
  • [ 10538-51-9 ]
  • [ 106-20-7 ]
  • N,N-bis(2-ethylhexyl) 3-(1,4-dimethoxyphen-2-yl)propenoic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 2,5-dimethoxycinnamic acid With Bromotrichloromethane; triphenylphosphine In dichloromethane for 0.75h; Reflux; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine In dichloromethane for 14h; Reflux; 2.1 N,N-Bis(2-ethylhexyl) 3-(1,4-dimethoxyphen-2-yl)propenoic acid amide To a solution of PPh3 (980 mg, 3.74 mmol) in dry CH2Cl2(12 mL) BrCCl3 (1.50 g, 7.66 mmol)was added. The resultingmixture was stirred at rt for 30 min, during which it turnedreddish-brown. Thereafter, 2,5-dimethoxycinnamic acid(4c, 700 mg, 3.37 mmol) was added, and the mixture washeated under reflux for 45 min. Thereafter, di(2-ethylhexyl)amine (1.62 g, 6.71 mmol) was added dropwise via a syringe,where the ensuing reaction is exothermic. The reactionmixture was stirred at reflux for 14 h. Then, thecooled mixture was concentrated in vacuo, and the residuewas subjected directly to column chromatography on asilica gel to give 5f (875 mg, 2.03 mmol, 60%) as a colorlessoil; nmax neat/cm1) 2961, 2877, 1660, 1622, 1506, 1489,1047, 772; dH (400 MHz, CDCl3) 1.00 (16H, m),1.48 (20H, m),1.69e1.79 (2H, m), 3.28e3.43 (4H, m), 3.77 (3H, s, OCH3),3.81 (3H, s, OCH3), 6.82 (1H, d, 3J 8.8 Hz), 6.84 (1H, d,3J 8.8 Hz), 7.00 (1H, s), 7.02 (1H, d, 3J 15.6 Hz), 7.86 (1H,d, 3J 15.6 Hz); dC (67.8 MHz, CDCl3, DEPT) 10.7 (CH3), 10.8(CH3), 14.0 (CH3), 14.1 (CH3), 23.1 (CH2, 2C), 23.7 (CH2), 24.0(CH2), 28.7 (CH2), 28.8 (CH2), 30.5 (CH2), 30.7 (CH2), 37.6 (CH), 40.0 (CH), 50.7 (CH2), 52.0 (CH2), 55.7 (OCH3), 56.0(CH3), 112.3 (CH), 114.4 (CH), 115.4 (CH), 119.6 (CH), 125.2(Cquat), 137.5 (CH), 152.8 (Cquat), 153.4 (Cquat), 167.3 (Cquat,CO).
  • 49
  • [ 106-20-7 ]
  • diethylenetriamine pentaacetic dianhydride [ No CAS ]
  • diethylenetriamine-N,N',N"-triacetic acid-N,N'-diacetic acid di(2-ethylhexyl)amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In 1,4-dioxane at 101℃; for 3h; 6 Next, 13.5 g (0.056 mol) of di (2-ethylhexyl) amine and 150 g of 1,4-dioxane were added to a 300 ml three-necked flask, and 10 g of diethylenetriamine pentaacetic dianhydride (0.028 Mol) was added.Thereafter, the reaction was carried out at a reaction temperature of 101 ° C. for 3 hours to obtain diethylenetriamine-N, N ', N "-triacetic acid-N, N'-diacetic acid di (2-ethylhexyl) amide
  • 50
  • [ 106-20-7 ]
  • ethylenediaminetetraacetic dianhydride [ No CAS ]
  • ethylenediamine-N,N'-diacetic acid-N,N'-diacetic acid di(2-ethylhexyl)amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In tetrahydrofuran at 66℃; for 3h; 4 Into a 300 ml three-necked flask, 18.8 g (0.078 mol) of di (2-ethylhexyl) amine and 150 g of hexane as a solvent were added and 10.0 g of ethylenediamine tetraacetic dianhydride (0.039 Mol) was added. Thereafter, the reaction was carried out at a reaction temperature of 69 ° C. for 6 hours to obtain the compound of the present invention. Further, the solvent was evaporated by concentrating under reduced pressure of 100 mmHg to obtain a yellow liquid. Elemental analysis results of the obtained liquid are shown in Table 1.
  • 51
  • [ 106-20-7 ]
  • [ 32315-10-9 ]
  • [ 1468-95-7 ]
  • C32H45NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: bis(trichloromethyl) carbonate; 9-hydroxymethylanthracene With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine In dichloromethane for 4h; Inert atmosphere; 3 Synthesis of ANT-DEHC As generally depicted in Scheme 3 above, triphosgene(2.137 g 0.5 eq.) suspended in anhydrous DCM(30 mL) under nitrogen atmosphere. The solution was cooled to 0° C. Then 9-(Hydroxymethyl)anthracene(3.0 g; 1.0 eq.) in anhydrous DCM(100 mL) and N,N-diisopropylethylamine(3.723 g; 2.0 eq.) were added. After stirring at RT for 3 h, bis(2-ethylhexyl)amine(3.478 g; 1.0 eq.) was slowly added and stirred for 4 h. The reaction mixture was washed by water and the organic phase is dried over sodium sulfate, filtered off and concentrated under reduced pressure. The crude title compound was purified by flash chromatography(EtOAc/heptane).
  • 52
  • [ 106-20-7 ]
  • [ 32315-10-9 ]
  • [ 612-25-9 ]
  • C24H40N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: bis(trichloromethyl) carbonate; 2-Nitrobenzyl alcohol With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine In dichloromethane for 4h; Inert atmosphere; 2 Synthesis of NB-DEHC(E) As generally depicted in the above Scheme 2, Triphosgene(1.16 g 0.3 eq.) suspended in anhydrous DCM(30 mL) under nitrogen atmosphere. The solution was cooled to 0° C. Then (2-nitrophenyl)methanol (2.0 g; 1.0 eq.) in anhydrous DCM(30 mL) and N,N-diisopropylethylamine (3.38 g; 2.0 eq.) were added. After stirring at RT for 3 h, bis(2-ethylhexyl)amine (3.15 g; 1.0 eq.) was slowly added and stirred for 4 h. The reaction mixture was washed by water and the organic phase is dried over sodium sulfate, filtered off and concentrated under reduced pressure. The crude title compound was purified by flash chromatography (EtOAc/heptane).
  • 53
  • [ 106-20-7 ]
  • N,N'-(para-phenylenedimethylene)bis(3-cyano-6-hydroxy-4-methyl-2-pyridone) [ No CAS ]
  • 3-methyl-4-(β-sulfatoethylsulfonyl)aniline [ No CAS ]
  • C47H61N7O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine; 3-methyl-4-(β-sulfatoethylsulfonyl)aniline With sodium hydroxide In water at 80℃; for 5h; Stage #2: With hydrogenchloride; sodium nitrite In water at 5 - 10℃; for 1.16667h; Stage #3: N,N'-(para-phenylenedimethylene)bis(3-cyano-6-hydroxy-4-methyl-2-pyridone) In water at 5 - 10℃; for 1h; 3- methyl-4 after the (β- sulfatoethyl sulfonyl) 29.3 parts of aniline were added to 350 parts of water, di (2-ethylhexyl) amine 24.1 parts and 12 parts of sodium hydroxide It was added and stirred for 5 hours at 80 .After cooling to room temperature, it was added concentrated hydrochloric acid 120 parts, were added dropwise 18 parts of a 40% aqueous sodium nitrite solution over 30 minutes at 5 to 10 ° C..After the dropwise addition, the mixture was stirred for 40 minutes at 5~10 , to destroy the excess of nitrous acid at sulfamic acid to obtain a diazotized. Couple component 40.2 parts of a diazo compound formula S (I-24), 300 parts of water, holding the pH = 7.0 to 8.0 with 10% sodium hydroxide aqueous solution of 10 parts of soda ash dropwise over 1 hour at 5 to 10 ° C., to obtain a first couple fluid.
  • 54
  • [ 50-00-0 ]
  • [ 3658-48-8 ]
  • [ 106-20-7 ]
  • bis(2-ethylhexyl) [bis(2-ethylhexyl)amino]methyl}phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: formaldehyd; 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With toluene-4-sulfonic acid In acetonitrile at 55℃; for 1h; Stage #2: bis(2-ethylhexyl)phosphite In acetonitrile at 80℃; for 6h; 2-Ethylhexyl hydrogen [bis(2-ethylhexyl)amino]-methyl}phosphonate (2). A mixture of 48.2 g (0.2 mol)of bis(2-ethylhexyl)amine, 6 g (0.2 mol) of paraformaldehyde,and 0.2 g (0.79 mmol) of p-toluenesulfonicacid in 120 mL of acetonitrile was stirred for 1 h at 55°C. Bis(2-ethylhexyl) phosphonate, 61.2 g (0.2 mol), wasthen added, and the mixture was stirred for 6 h at 80°C.According to the 31P NMR data, the mixture containedbis(2-ethylhexyl) [bis(2-ethylhexyl)amino]methyl}phosphonate(1, δP 26.04 ppm) as the only product.
  • 55
  • [ 106-20-7 ]
  • [ 632-22-4 ]
  • C21H47N3*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
47 g Stage #1: tetramethylurea With trichlorophosphate In toluene at 60 - 65℃; for 2h; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In toluene at 0 - 20℃; Preparation of the Hexaalkylguanidinium Chloride (C2a) Preparation of the Hexaalkylguanidinium Chloride (C2a) (0080) (0081) To a solution of 15.5 mL (0.13 mol) of tetramethylurea in 60 mL of toluene are added dropwise, at 60-65° C., 13 mL (0.13 mol) of phosphoryl chloride. After stirring for two hours, the mixture is cooled and, at 0-5° C., a mixture of 18 mL of triethylamine and 40 mL (0.14 mol) of bis(2-ethylhexyl)amine in 30 mL of toluene is added dropwise. Subsequently, the temperature is allowed to rise to about 20° C., and stirring is continued overnight. Then the pale yellow mixture is admixed with 54 mL of NaOH (30% by weight) while cooling. The mixture is stirred together with 150 mL of NaCl solution. The toluene phase is separated off and dried with magnesium sulfate, and the solvent is removed under reduced pressure. This gives 47 g of a pale beige, waxy solid.
  • 56
  • [ 106-20-7 ]
  • 1-(3-bromopropyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)imide [ No CAS ]
  • 1-(3-di(2-ethylhexyl)aminopropyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)imide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In acetonitrile for 30h; Inert atmosphere; Reflux; Synthesis of 1,3- (di (2-ethylhexyl) aminopropyl) -3-methylimidazolium bis (trifluoromethanesulfonyl) imide] ("Compound C2-6") 4.84 g (10 mmol) of compound 2, 7.24 g (30 mmol) of di (2-ethylhexyl) amine and 50 mL of acetonitrile (CH 3 CN) were added to a three-necked round bottom flask (100 mL) and the inside of the flask was purged with argon. Thereafter, the reaction solution was heated and refluxed for 30 hours in an oil bath set at 85 ° C., and the reaction was carried out. The reaction solution was concentrated under reduced pressure using a rotary evaporator until solids were precipitated. After that, the liquid separation operation was carried out six times with chloroform (CHCl 3) / saturated sodium bicarbonate aqueous solution (sat. NaHCO 3 aq.), The saturated sodium hydrogencarbonate aqueous phase of the upper phase was removed and the lower phase chloroform phase was taken out . Subsequently, a liquid separation operation was performed with chloroform (CHCl 3) / water (H 2 0), and the lower phase chloroform phase was washed. The chloroform solution was subjected to a dehydration operation using anhydrous magnesium sulfate (MgSO 4), filtration through celite, concentration under reduced pressure using a rotary evaporator and a vacuum dryer. The separated liquid / hexane was further subjected to liquid separation operation to wash the ionic liquid phase. The ionic liquid was concentrated under reduced pressure using a rotary evaporator and vacuum dryer. In this way, the compound C2-6 (C25 H4 6 F 6 N 4 O 4 S 2) was obtained in a yield of 80% (5.16 g, 8.0 mmol).
  • 57
  • [ 106-20-7 ]
  • [ 3972-56-3 ]
  • 4-(tert-butyl)-N,N-bis(2-ethylhexyl)aniline [ No CAS ]
  • 58
  • [ 50-00-0 ]
  • [ 106-20-7 ]
  • [bis(2-ethylhexyl)amino]methyl}phosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With phosphonic Acid Acidic conditions; Reflux; 3 [bis(2-ethylhexyl)amino]methyl}phosphonic acid (BEAAP) Di (2-ethylhexyl) amine and The phosphorous acid was placed in a three-necked flask. Formaldehyde was slowly added dropwise under acidic conditions and refluxed. Thereafter, the mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. Chloroform was added to the obtained residue, and washing was sufficiently carried out. The organic phase was dehydrated with magnesium sulfate. After distilling off the solvent under reduced pressure, the product was dried under reduced pressure.
  • 59
  • [ 50-00-0 ]
  • [ 106-20-7 ]
  • [ 27231-36-3 ]
  • C33H70N2 [ No CAS ]
  • C42H78N4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 90℃; for 4h; 10 Example 10: Synthesis of 2-Mercaptobenzimidazole Alkyl Derivatives (0278) [0134] 5-Methyl-2-mercaptobenimidzole ( 20.00 g, 0.122 moles), di-(2- ethylhexyl)amine ( 61 .76 g, 0.256 moles), HAN ( 121 .80 g, 57 wt.%), and (0279) paraformaldehyde ( 7.94 g, 0.243 moles) were mixed in a 500 mL round bottom flask. The reaction mixture was stirred for 4 hours at 90 °C. During this time the mixture clarified and water was generated. A sample was removed and examined for clarity at 25 and 0 °C. The sample was not clear and thus failed. [0135] The reaction temperature was increased to 105 °C and a nitrogen sweep was applied to remove any water that had been generated. Samples were removed every 30 minutes and monitored for clarity at 25 and 0 °C. Samples collected after (0280) approximately 1 hour or when approximately 5.6 wt.% condensate, i.e., water, had been removed passed, i.e., the samples were clear. (0281) [0136] After a clear sample was obtained, the reaction mixture was cooled to 45 °C and alkyl mercapto-thiadiazole (24.6 wt.%) and HAN (1 1 .52 wt.%) were added to the mixture and blended. (0282) 0137] The reaction product is identified hereinafter as Product J
  • 60
  • [ 50-00-0 ]
  • [ 106-20-7 ]
  • [ 134469-07-1 ]
  • C41H76N4S [ No CAS ]
  • C33H70N2 [ No CAS ]
  • C24H41N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene at 20℃; Overall yield = 86.6 g; 3 Example 3: Synthesis of 2-Mercaptobenzimidazole Alkyl Derivatives (0245) [0116]2-Mercaptobenzimidazole (10 g, 66.58 mol) was added to bis(2- ethylhexyl)amine (32.16 g, 133.2 mmoles) in a 500 mL round bottom flask. Toluene (46.14 g) was added, followed by the drop wise addition of formalin (4.0 g, 133.2 mmoles). The reaction was stirred overnight at room temperature. The reaction mixture was poured into a separatory funnel and the organic layer was collected and dried with Na2S04 to yield the resulting product (86.6 g) as 50% active in solution. (0246) [0117] The reaction can also be performed in a similar amount of HAN instead of toluene. (0247) [0118] The reaction products are identified hereinafter as Product B.
  • 61
  • [ 50-00-0 ]
  • [ 106-20-7 ]
  • [ 2349-67-9 ]
  • C33H70N2 [ No CAS ]
  • C53H108N6S2 [ No CAS ]
  • C36H73N5S2 [ No CAS ]
  • C19H38N4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In Triethylene glycol dimethyl ether at 20℃; Overall yield = 29 g; 7 Example 7: Synthesis of Thiadiazole Alkyl Derivatives [0128] 5-Amino-1 ,3,4-thiadiazole-2-thiol (2.15 g, 14.7 mmoles) was added to bis-2- ethylhexylamine (10.6 g, 44.1 mmoles) in a 250 ml_ round bottom flask. Triglyme (15 ml_) was added, followed by the drop wise addition of formalin (3.6 g, 44.1 mmoles). The reaction was stirred overnight at room temperature. The reaction mixture was poured into a separatory funnel and the organic layer was collected and dried with Na2S04 to yield the resulting product (29 g) as 50% active in solution. (0266) [0129] The reaction products are identified hereinafter as Product G.
  • 62
  • [ 106-20-7 ]
  • [ 69-72-7 ]
  • bis(2-ethylhexyl)ammonium salicylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.80g at 20℃; for 1h; 8 synthesis of example 8 2.42 g (10mmo1) of bis(2-ethylhexyl)amine and the salicylic acid 1.38g (10mmol) were measured, respectively, and it taught the reaction container. Contents were stirred and mixed at the room temperature for 1 hour, and 3.80 g of bis(2-ethylhexyl)ammonium salicylate (the chemical formula 8, a light yellow liquid) was obtained.
  • 63
  • [ 5435-64-3 ]
  • [ 106-20-7 ]
  • [ 3011-82-3 ]
  • C41H86NOP [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% at 140℃; for 72h; I.I.5 I.5-Compound ODODEHATMHP: The title compound, which corresponds to thegeneral formula (I) in which R’rrrR2=n-octyl, R3=2,4,4-trimethylpentyl, R4=H, R5rrrR6=2-ethylhexyl, is synthesised by implementing step A, from di-n-octylphosphineoxide (7.6 mmol), 3,5,5-trimethylhexanal and di(2-ethyl-hexyl)amine (reflux for 72 hours at 140° C.).10101] Yield: 72% (5.5 mmol)10102] 3’P NMR (162 MHz, CDC13, 25° C.) ö(ppm): 52.910103] ‘H NMR (400 MHz, CDC13, 25° C.) ö(ppm): 2.87(m, JP-H=8.4 Hz, 1H, P-CH(Oct)-N); 2.68 (m, 2H,N-CH2-CH); 2.38 (m, 2H, N-CH2----CH); 1.87-1.5 1 (m,1OH); 1.48-1.08 (m, 41H); 0.96-0.79 (m, 30H, CH3)10104] ‘3C NMR (100 MHz, CDC13, 25° C.) ö(ppm): 57.6& 56.9 (d, J=65.3 Hz, P-CH-N); 52.5; 52.2(N-CH2); 39.1; 38.5; 38.4; 38.2; 28.0; 27.5; 22.4 (CH);36.8; 36.5; 35.9; 34.9; 32.0; 31.8; 31.4; 31.2; 28.0; 27.5;24.7; 24.4; 23.5; 22.8; 22.1 (CH2); 30.6; 30.5; 21.8; 21.7;14.3; 14.2; 11.1; 11.0; 10.9 (CH3)
  • 64
  • [ 124-19-6 ]
  • [ 106-20-7 ]
  • [ 195195-90-5 ]
  • C41H86NOP [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% at 140℃; for 8h; I.I.3 I.3-Compound ODEHDEHANP: The title compound, which corresponds to thegeneral formula (I) in which R’rrrR2=2-ethylhexyl, R3=n-octyl, R4=H, R5rrrR6=2-ethylhexyl, is synthesised byimplementing step A, from di(2-ethylhexyl)phosphine oxide(2.7 mmol), n-nonanal and di(2-ethylhexyl)amine (reflux for8 hours at 140° C.).10089] Yield: 27% (0.65 mmol)10090] 3’PNMR (162 MHz, CDC13, 25° C.) ö(ppm): 51.610091] ‘H NMR (400 MHz, CDC13, 25° C.) ö (ppm): 2.84(m, 2H, PCH(CH(C2H5)-C5H,3)---N); 2.34 (m, 2H);1.88-1.07 (m, 55H); 0.92-0.78 (m, 27H, CH3) HR-ESI-MS:calculated for C4,H87NOP=640.6525. found=640.65 13.
  • 65
  • [ 124-19-6 ]
  • [ 106-20-7 ]
  • [ 3011-82-3 ]
  • C41H86NOP [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% at 140℃; for 24h; I.I.2 I.2-Compound ODODEHANP: The title compound, which corresponds to the general formula (I) in which R’rrrR2rrrR3=n-octyl, R4=H, R5rrrR62-ethylhexyl, is synthesised by implementing step A, from di-n-octylphosphine oxide (4.4 mmol), n-nonanaland di(2-ethylhexyl)amine (reflux for 24 hours at 140° C.).10082] Yield: 69% (3.2 mmol)10083] 3’P NMR (162 MHz, CDC13, 25° C.) ö(ppm): 53.010084] ‘H NMR (400 MHz, CDC13, 25° C.) ö(ppm): 2.44(m, JFH=8.4 Hz, 1H, P-CH(Oct)-N); 2.58 (m, 2H,N-CH2-CH); 2.37 (m, 2H, N-CH2---CH); 1.90 (m, 2H);1.86-1.50 (m, 1OH); 1.42-1.11 (m, 48H); 0.91-0.78 (m, 21H,CH3)10085] ‘3C NMR (100 MHz, CDC13, 25° C.) ö (ppm): 60.3& 59.7 (d, J=66.7 Hz, P-CH---N); 57.2 (N-CH2); 38.2(CH-CH2-N); 31.9; 31.4; 31.3; 31.2; 31.1; 29.9; 29.6;29.5; 29.3; 29.1; 25.6; 24.5; 24.3; 24.1; 23.3; 23.1; 22.7;22.1; 21.9 (CH2); 14.1; 10.9; 10.7 (CH3)10086] HR-ESI-MS: calculated for C4,H87NOP=640.6525. found=640.6495.
  • 66
  • [ 106-20-7 ]
  • [ 106-43-4 ]
  • C23H41N [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With C46H56Cl2N3O2PPd; potassium <i>tert</i>-butylate In 1,2-dimethoxyethane at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube;
  • 67
  • [ 106-20-7 ]
  • [ 7051-16-3 ]
  • N,N-bis(2-ethylhexyl)-3,5-dimethoxyaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
  • 68
  • [ 106-20-7 ]
  • [ 22034-13-5 ]
  • C22H37N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium tert-butylate; In toluene; at 120℃; for 5h;Inert atmosphere; To a flask equipped with a reflux device, 3.3 g (29.0 mmol) of t-butoxypotassium, 0.3 g (0.5 mmol) of PEPPSI?-IPr (manufactured by Sigma-Aldrick corporation, product name) as a Pd catalyst, 150 mL of toluene, 5.2 g (24.1 mmol) of the compound (b), and 8.0 mL (26.5 mmol) of bis(2-ethylhexyl)amine were added, and it was refluxed at 120° C. for five hours under a nitrogen atmosphere. After a reaction was finished, solids in a reaction solution were removed by filtration, the filtrate was condensed, and then refinement was performed by column chromatography using hexane/ethyl acetate (99:1, volume ratio) as a developing solution, to thereby obtain a compound (c) (5.3 g, 14 mmol, yield: 58percent).
  • 69
  • [ 34784-04-8 ]
  • [ 106-20-7 ]
  • C25H40N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium <i>tert</i>-butylate In toluene at 125℃; for 5h; (Production of Compound (i)) To a flask, 2.08 g (10 mmol) of 5-bromoisoquinoline, 10 mL of toluene, 2.65 g (11 mmol) of bis(2-ethylhexyl)amine, 0.13 g (0.2 mmol) of a Pd catalyst (PEPPSI-IPr), and 1.34 g (12 mmol) of t-butoxypotassium were added, and a reaction was carried out at 120° C. for five hours. After the reaction was finished, solids in a reaction solution were removed by filtration, the filtrate was condensed, and then refinement was performed by a column chromatography method. As a result, a compound (i) (1.36 g, 3.7 mmol, yield: 37%) was obtained.
  • 70
  • [ 106-20-7 ]
  • [ 437-81-0 ]
  • C23H38FNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 72h; To a flask, 12.7 g (52.8 mmol) of di(2-ethylhexyl)amine, 10 mL of N,N-dimethylfolmamide (DMF), and 7.3 g (52.8 mmol) of potassium carbonate were added, it was stirred at room temperature, and further 5 g (35.1 mmol) of 2,6-difluorobenzaldehyde was added. An oil bath was used to set a reaction temperature at 80° C., and the resultant was stirred for three days. The reaction temperature was returned to room temperature, 30 mL of water was added and stirred, and 50 mL each of ethyl acetate and hexane were added. An organic layer was dried with anhydrous magnesium sulfate, a solvent was removed under reduced pressure, and then refinement was performed by column chromatography using hexane/ethyl acetate (9:1, volume ratio) as a developing solution, to thereby obtain a compound (u) (8.8 g, 24.2 mmol, yield: 69%).
  • 71
  • [ 106-20-7 ]
  • [ 88284-48-4 ]
  • 2-(bis(2-ethylhexyl)amino)benzenesulfonyl fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With potassium fluoride; fluorosulfonyl fluoride; 18-crown-6 ether In tetrahydrofuran at 25℃; for 24h; Schlenk technique;
  • 72
  • [ 106-20-7 ]
  • [ 17295-26-0 ]
  • 6-hydroxy-2-naphthoic acid-N-bis(2-ethylhexyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 6-acetoxy-2-naphthoic acid With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 50℃; for 2h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In tetrahydrofuran at 20 - 60℃; for 2.66667h; Inert atmosphere; Stage #3: With sodium hydroxide In water at 50℃; for 6h; Inert atmosphere; 3 Example 3 In a 3.0 L 4-neck flask equipped with a stirrer, temperature sensor and reflux tube,200 g (0.87 mol) of 6-acetoxy-2-naphthoic acid, 113 g of thionyl chloride(0.95 mol), 0.8 g of DMF and 800 g of THF were added, and the mixture was heated to 50 ° C. under a nitrogen stream and stirred for 2 hours. After completion of the stirring, the reaction solution was cooled to room temperature and THF was distilled off by reducing the pressure to 60 mmHg.Thereto, 800 g of THF was added again, and 87.9 g (0.86 mol) of triethylamine was dropped while stirring at room temperature under a nitrogen stream. continue,Diethylhexylamine 209 gWas added dropwise over 100 minutes. It heated up to 60 degreeC and stirred at the same temperature for 1 hour. Then 60The hot filtration was performed with the temperature kept unchanged.The obtained filtrate is transferred to a 3.0 L four-necked flask, and 108 g of 48% aqueous NaOH solution andAfter 800 g of water was added, the temperature was raised to 50 ° C. under a nitrogen stream and the mixture was stirred for 6 hours. After stirring is complete,Cool to room temperature and add 70% sulfuric acid until the pH of the solution is 7. Then rise to 50 ° CWarm, wash and extract the organic layer.The obtained organic layer is transferred to a 3.0 L four-necked flask, and the remaining diethylhexylamine is distilled off under reduced pressure at 110 ° C. and 3 Torr.As a viscous liquid281 g of 6-hydroxy-2-naphthoic acid-N-diethylhexylamide was obtained (yield 78 mol%, purity 94.1)%).
  • 73
  • [ 106-20-7 ]
  • C21H29BF2N2O2 [ No CAS ]
  • C37H62BF2N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.5h;
  • 74
  • [ 106-20-7 ]
  • [ 18880-00-7 ]
  • N-(4-(tert-butyl)benzyl)-2-ethyl-N-(2-ethylhexyl)hexan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; N-(4-(tert-butyl)benzyl)-2-ethyl-N-(2-ethylhexyl)hexan-1-amine (7g) To a solution of di(2-ethylhexyl)amine (966 mg, 4.40 mmol) in MeCN (20 mL) was addedN,N-diisopropylethylamine (775 mg, 6.00 mmol) and 4-tert-butylbenzylbromide (999 mg, 4.00mmol) under argon atmosphere. After stirring for 24 h at room temperature, the solvents wereevaporated under reduced pressure. The crude product was purified by silica gel columnchromatography (hexane:EtOAc = 50:1) to give the title compound (1.20 g, 77%) as a colorless oil;
  • 75
  • [ 106-20-7 ]
  • [ 98-74-8 ]
  • C22H38N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
279 g With triethylamine In toluene at 10 - 20℃; for 21h; 1 Synthesis Example 1 Synthesis of nitro compound (intermediate 1) p-Nitrophenylsulfonyl chloride (140 g, 0.63 mol) and toluene (800 mL) were added to 3 L kolben, and dissolved.Triethylamine (127.9 g, 1.26 mol) was added. After cooling to 10 ° C., di (2-ethylhexyl) amine (152.6 g, 0.63 mol) was added dropwise over 1 hour. After stirring at 10 ° C. for 1 hour, the mixture was stirred at room temperature for 20 hours. Water (500 mL) was added, and the mixture was washed and separated. The organic layer was washed with 1M HCl (500mL × 2), water (500 mL × 2), and saturated saline (500 mL) in that order, and then dried over magnesium sulfate (50 g). After the solid was separated by filtration, the solvent was distilled off to obtain a compound represented by the formula (intermediate 1) in the reaction formula (2) as a brown oil (279.0 g, Y = 103.5%, HPLC purity 96.1%)
  • 76
  • [ 75-15-0 ]
  • [ 106-20-7 ]
  • [ 1072-71-5 ]
  • C36H68N4S5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.2% Stage #1: carbon disulfide; 2-ethyl-N-(2-ethylhexyl)-1-hexanamine; 2,5-Dimercapto-1,3,4-thiadiazole With sodium ethanolate In 2-methyl-propan-1-ol at -50℃; for 5h; Stage #2: With sodium molybdate In 2-methyl-propan-1-ol at 160℃; for 8h; Sealed tube; Inert atmosphere; 3.1; 3.2; 3.3; 3.4 (1) Add 200 mL of isobutanol and 102 g of sodium ethoxide to the reaction kettle, and add 38 g of DMTD in batches with stirring to fully dissolve;(2) Add 133g of diisooctylamine to the reaction kettle, mix well, add 33mL of carbon disulfide dropwise at -50 ° C; after the dropwise addition, react for 5h;(3) Add 2 g of sodium molybdate to the reaction kettle, pressurize the sealed nitrogen to 0.6 MPa, raise the temperature to 160 ° C, and react for 8 hours;(4) Cool the reaction system to room temperature, filter, wash with water, separate the oil layer, and evaporate the low boilers to obtain the product with a yield of 85.2%.The thiadiazole group-containing lubricant additive C,Among them, R1 and R2 are both isooctyl (C8 has a branched alkyl group), and the ICP elemental analysis S content is 22.9% (theoretical S content is 22.3%).
  • 77
  • [ 124-13-0 ]
  • [ 106-20-7 ]
  • N,N-di(2-ethylhexyl)-n-octylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With 5%-palladium/activated carbon; hydrogen at 120℃; for 14h; 2 [Synthesis Example 2] Synthesis of N, N-di (2-ethylhexyl) -n-octylamine Into a 500 ml autoclave,152.1 g of di (2-ethylhexyl) amine, 88.8 g of n-octanal,Charge 3.0 g of 5% Pd / C catalyst (1.4 g dry weight),The inside of the autoclave was replaced with nitrogen.Then after substituting with hydrogen,Hydrogen was introduced with stirring to adjust the internal pressure to 0.4 MPa, and then the temperature was raised.After the temperature inside the autoclave reached 120 ° C,Further, hydrogen was introduced to adjust the internal pressure to 0.8 MPa.Hydrogen is consumed as the reaction progresses, so while adding hydrogen successively to maintain the internal pressure at 0.8 MPa,The reaction was carried out (reaction time 14 hours).After the reaction is completed, the reaction solution is cooled to 25 ° C,The catalyst was filtered off by filtration.After adding 37.1 g of ion-exchanged water to the obtained filtrate, heating to 143 ° C.,After distilling off water and low boiling impurities,Purified by distillation,As a fraction having a boiling point of 189 to 200 ° C./0.03 kPa,98.9% pure128 g (yield 57%) of N, N-di (2-ethylhexyl) -n-octylamine was obtained. The results of 1H-NMR analysis of N, N-di (2-ethylhexyl) -n-octylamine are shown below.
  • 78
  • [ 104-76-7 ]
  • [ 104-75-6 ]
  • [ 106-20-7 ]
YieldReaction ConditionsOperation in experiment
With chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II); urea; diphenylphosphinopropane In diethylene glycol dimethyl ether at 160℃; for 12h; Autoclave; Inert atmosphere; 2.3. General catalytic procedure for amination General procedure: The autoclave was charged with 1-hexylalcohol (2.5 mmol) and urea (2.5 mmol) in 1mLdiglyme. [(Cp)RuCl(dppe)] (3% mol) as catalyst, diphenylphosphinopropane (dppp)(0.07 mmol) as supporting ligand and 0.04 g K2CO3 as base was added. The autoclavewas closed, flushed with argon for 5 min and then temperature was adjusted at160 °C. After 12 h, the autoclave was cooled to room temperature and the productswere analyzed by gas chromatography.
  • 79
  • [ 106-20-7 ]
  • phenyl (4-methoxybenzoyl)oxycarbamate [ No CAS ]
  • 3-((4-methoxybenzoyl)oxy)-1,1-bis(2-ethylhexyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With 1H-imidazole In tetrahydrofuran at 100℃; for 2h; Microwave irradiation; Sealed tube;
  • 80
  • [ 106-20-7 ]
  • [ 1453099-10-9 ]
  • C33H28N2O6S2*C16H35N [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 7,11-dipropyl-7,11-dihydro-17cH-benzo[a]benzo[5,6]quinolino[2,3,4-kl]acridin-17c-ylium tetrafluoroborate With sulfuric acid at 20℃; for 48h; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine In dichloromethane; water regioselective reaction;
  • 81
  • [ 106-20-7 ]
  • [ 421-83-0 ]
  • bis(2-ethylhexyl)carbamothioic fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With triphenylphosphine; sodium iodide In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;
  • 82
  • [ 75-15-0 ]
  • [ 106-20-7 ]
  • C2H2Mo2N2O6S3 [ No CAS ]
  • C36H68Mo2N4O4S7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.6% In butan-1-ol at 40 - 60℃; for 5h; 3.3; 3.4 (3) Disperse the intermediate obtained in step (2) in 100 mL of n-butanol, add 133 g of bis(2-ethylhexyl)amine, mix, and add 33 mL of carbon disulfide dropwise, and control the temperature of the reaction system at 40°C during the dropping process; after the addition, continue to react at 40°C for 1h; the reaction system was heated to 60°C and heated to reflux for 4 hours; (4) after the reaction, the solvent is evaporated to obtain the product containing molybdenum thiadiazole derivative C, wherein R1 and R2 are both isooctyl groups (C8 branched alkyl), and the theoretical molybdenum content is 18.5%; finally, 209 g of product was obtained by weighing, the calculated yield was 80.6%, and the measured molybdenum content was 18.5%.
  • 83
  • [ 75-15-0 ]
  • [ 106-20-7 ]
  • molybdenyl acetylacetonate [ No CAS ]
  • C34H68MoN2O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.56% In ethanol at 20℃; for 12h; 4 This embodiment provides a preparation method of dialkyldithioorganomolybdenum, which includes the following steps: Under stirring, add 3.26g molybdenum acetylacetonate MoO2(acac)2 to 2.60g of di-n-butylamine in absolute ethanol solution, and add 0.76g CS2(di-n-butylamine, molybdenum acetylacetonate and The molar ratio of CS2 is 2:1:2). After the dropwise addition is completed, the reaction is carried out at room temperature for 12 hours. After the reaction was terminated, the solvent was removed under reduced pressure to obtain 5.16 g of a brownish-red oily paste of molybdenum dialkyldithiocarbamate (MoDTC4) with a yield of 95.56%, of which the content of molybdenum was 14.35%.
  • 84
  • [ 106-20-7 ]
  • C9H10O4S [ No CAS ]
  • C25H43NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran; dichloromethane at 20℃; 12 [Synthesis of A2-4-3] To a dichloromethane solution (200 mL) of A2-4-2 (8.96 g, 41.8 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (9.8 g, 51 mmol), a tetrahydrofuran solution (190 mL) of 1-hydroxybenzotriazole monohydrate (7.8 g, 51 mmol) was added. Furthermore, a tetrahydrofuran solution (10 mL) of triethylamine (7.6 mL, 55 mmol) and bis(2-ethylhexyl)amine (12.6 mL, 42.0 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure and after adding dichloromethane (150 mL washed with an aqueous sodium hydrogencarbonate solution and water. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain A2-4-3 (18.9 g, 43.3 mmol, 103% yield) as a crude product. The crude product was used for the next reaction without being purified.
  • 85
  • [ 106-20-7 ]
  • 2-bromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene [ No CAS ]
  • C41H71NS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.02% Stage #1: 2-bromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene With magnesium In tetrahydrofuran at -40℃; for 3h; Inert atmosphere; Reflux; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With N-chloro-succinimide In tetrahydrofuran; toluene at -40℃; for 0.333333h; Inert atmosphere; Stage #3: With titanium(IV) isopropylate at 20℃; for 3h; 3.A3-2 <STEP A3-2> Intermediate A3-1 (1.5 g, 4.15 mmol) obtained in step A3-1 and magnesium turnings (0.202 g, 8.30 mmol) were put into a flask and dissolved in anhydrous tetrahydrofuran (6 ml) under a nitrogen atmosphere. The resulting solution was refluxed for 3 hours and cooled to -40° C. In another flask, N-chlorosuccinimide (0.554 g, 4.15 mmol) was dissolved in anhydrous toluene (20 ml) under a nitrogen atmosphere, and bis-(2-ethylhexyl)amine (1.00 g, 4.15 mmol) was added thereto, followed by stirring for 20 minutes.Tetraisopropyl orthotitanate (0.554 g, 4.15 mmol) was added dropwise to the mixed solution cooled to -40° C. and stirred for 5 minutes. After stirring, the mixed solution of N-chlorosuccinimide and bis-(2-ethylhexyl)amine was added dropwise, followed by stirring at room temperature for 3 hours. After the completion of reaction, a saturated aqueous potassium carbonate solution (8 ml) was added, and subsequently, the mixture was diluted with ethyl acetate and filtered. The resulting solution was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine. The solvent was removed, and Intermediate A3-2 (0.187 g, yield: 7.02%) was obtained by silica gel column chromatography (hexane:triethylamine=100:3).
  • 86
  • [ 106-20-7 ]
  • 2-bromo-4,4-diphenyl-4Hcyclopenta[1,2-b:5,4-b']dithiophene [ No CAS ]
  • C37H47NS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
27.5% Stage #1: 2-bromo-4,4-diphenyl-4Hcyclopenta[1,2-b:5,4-b']dithiophene With magnesium In tetrahydrofuran at -40℃; for 3h; Inert atmosphere; Reflux; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With N-chloro-succinimide In tetrahydrofuran; toluene for 0.333333h; Inert atmosphere; Stage #3: With titanium(IV) isopropylate In tetrahydrofuran; toluene at 20℃; for 3h; 5.A5-5 <Step A5-5> Intermediate A5-4 (3.50 g, 8.55 mmol) obtained in step A5-4 and magnesium turnings (0.416 g, 17.1 mmol) were put into a flask and dissolved in anhydrous tetrahydrofuran (20 ml) under a nitrogen atmosphere. The resulting solution was refluxed for 3 hours and cooled to -40° C. In another flask, N-chlorosuccinimide (1.03 g, 7.70 mmol) was dissolved in anhydrous toluene (20 ml) under a nitrogen atmosphere, and bis-(2-ethylhexyl)amine (1.86 g, 7.70 mmol) was added, followed by stirring for 20 minutes.Tetraisopropyl orthotitanate (2.43 g, 8.55 mmol) was added dropwise to the mixed solution cooled to -40° C. and after stirring for 5 minutes, the mixed solution of N-chlorosuccinimide and bis-(2-ethylhexyl)amine was added dropwise thereto, followed by stirring at room temperature for 3 hours. After the completion of reaction, a saturated aqueous potassium carbonate solution (17 ml) was added, and subsequently, the mixture was diluted with ethyl acetate and filtered. The resulting solution was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine. The solvent was removed, and Intermediate A5-5 (1.34 g, yield: 27.5%) was obtained by silica gel column chromatography (hexane:triethylamine=100:3).
  • 87
  • [ 106-20-7 ]
  • C37H45BrS2 [ No CAS ]
  • C53H79NS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
4% Stage #1: C37H45BrS2 With magnesium In tetrahydrofuran at -40℃; for 3h; Reflux; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With N-chloro-succinimide In toluene for 0.333333h; Inert atmosphere; Stage #3: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With titanium(IV) isopropylate; N-chloro-succinimide 6.A6-7 <Step A6-7> Intermediate A6-6 (6.00 g, 9.47 mmol) obtained in step A6-6 and magnesium turnings (0.460 g, 18.9 mmol) were put into a flask and dissolved in anhydrous tetrahydrofuran (14 ml) under a nitrogen atmosphere. The resulting solution was refluxed for 3 hours and cooled to -40° C. In another flask, N-chlorosuccinimide (1.14 g, 8.53 mmol) was dissolved in anhydrous toluene (21 ml) under a nitrogen atmosphere, and bis-(2-ethylhexyl)amine (2.06 g, 8.53 mmol) was added, followed by stirring for 20 minutes. Tetraisopropyl orthotitanate (2.69 g, 9.47 mmol) was added dropwise to the mixed solution cooled to -40° C. and after stirring for 5 minutes, and then the mixed solution of N-chlorosuccinimide and bis-(2-ethylhexyl)amine was added dropwise thereto, followed by stirring at room temperature for 3 hours. After the completion of reaction, a saturated aqueous potassium carbonate solution (19 ml) was added, and subsequently, the mixture was diluted with ethyl acetate and filtered. The resulting solution was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine. The solvent was removed, and Intermediate A6-7 (0.303 g, yield: 4.0%) was obtained by silica gel column chromatography (hexane:triethylamine=100:3).
  • 88
  • [ 106-20-7 ]
  • C17H21BrS2 [ No CAS ]
  • C33H55NS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% Stage #1: C17H21BrS2 With magnesium In tetrahydrofuran at -40℃; for 3h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With N-chloro-succinimide In tetrahydrofuran; toluene for 0.333333h; Inert atmosphere; Stage #3: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With titanium(IV) isopropylate; N-chloro-succinimide In tetrahydrofuran; toluene 7.A7-5 <Step A7-5> Intermediate A7-4 (4.31 g, 11.7 mmol) obtained in step A7-4 and magnesium turnings (0.85 g, 35.0 mmol) were put into a flask and dissolved in anhydrous tetrahydrofuran (17 ml) under a nitrogen atmosphere. The resulting solution was refluxed for 3 hours and cooled to -40° C. In another flask, N-chlorosuccinimide (1.40 g, 10.5 mmol) was dissolved in anhydrous toluene (28 ml) under a nitrogen atmosphere, and bis-(2-ethylhexyl)amine (2.53 g, 10.5 mmol) was added thereto, followed by stirring for 20 minutes.Tetraisopropyl orthotitanate (3.32 g, 11.7 mmol) was added dropwise to the mixed solution cooled to -40° C. and after stirring for 5 minutes, the mixed solution of N-chlorosuccinimide and bis-(2-ethylhexyl)amine was added dropwise thereto, followed by stirring at room temperature for 3 hours. After the completion of reaction, a saturated aqueous potassium carbonate solution (24 ml) was added thereto, and subsequently, the mixture was diluted with ethyl acetate and filtered. The resulting solution was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine. The solvent was removed, and Intermediate A7-5 (0.76 g, yield: 12%) was obtained by silica gel column chromatography (hexane:triethylamine=100:3).
  • 89
  • [ 4653-08-1 ]
  • [ 106-20-7 ]
  • C24H41NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran; dichloromethane at 20℃; 9 [Synthesis of A2-1-3] To a dichloromethane solution (350 mL) of A2-1-2 (15.4 g, 83.3 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (19.2 g, 100 mmol), a tetrahydrofuran solution (190 mL) of 1-hydroxybenzotriazole (13.5 g, 100 mmol) was added. Furthermore, a tetrahydrofuran solution (10 mL) of triethylamine (15.1 mL, 108 mmol) and bis(2-ethylhexyl)amine (25.0 mL, 83.3 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure and after adding dichloromethane (150 mL), washed with an aqueous sodium hydrogencarbonate solution and water. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain A2-1-3 (34.8 g, 85.4 mmol, 103% yield) as a crude product. The crude product was used for the next reaction without being purified.
  • 90
  • [ 39712-64-6 ]
  • [ 106-20-7 ]
  • C25H43NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran; dichloromethane at 20℃; 10 [Synthesis of A2-2-3] To a dichloromethane solution (60 mL) of A2-2-2 (2.69 g, 13.6 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (3.10 g, 16.2 mmol), a tetrahydrofuran solution (50 mL) of 1-hydroxybenzotriazole monohydrate (2.48 g, 16.2 mmol) was added. Furthermore, a tetrahydrofuran solution (10 mL) of triethylamine (2.44 mL, 17.5 mmol) and bis(2-ethylhexyl)amine (4.04 mL, 13.5 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure and after adding dichloromethane (50 mL), washed with an aqueous sodium hydrogencarbonate solution and water. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain A2-2-3 (5.88 g, 13.9 mmol, 103% yield) as a crude product. The crude product was used for the next reaction without being purified.
  • 91
  • [ 106-20-7 ]
  • C10H12O3S [ No CAS ]
  • C26H45NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran; dichloromethane at 20℃; 11 [Synthesis of A2-3-3] To a dichloromethane solution (200 mL) of A2-3-2 (8.00 g, 37.7 mmol) and 1-(3-dimethyl aminopropyl)-3-ethyl carbodiimide hydrochloride (8.72 g, 45.5 mmol), a tetrahydrofuran solution (130 mL) of 1-hydroxybenzotriazole monohydrate (6.94 g, 45.3 mmol) was added. Furthermore, a tetrahydrofuran solution (10 mL) of triethylamine (7.0 mL, 50 mmol) and bis(2-ethylhexyl)amine (11.5 mL, 38.3 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure and after adding dichloromethane (100 mL), washed with an aqueous sodium hydrogencarbonate solution and water. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain A2-3-3 (17.33 g, 39.8 mmol, 106% yield) as a crude product. The crude product was used for the next reaction without being purified
  • 92
  • [ 108-77-0 ]
  • [ 106-20-7 ]
  • [ 150771-77-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetone for 2h; Cooling with ice; 2 Example 2 Put 0.05mol (9.25g) cyanuric chloride,0.06mol (8.30g) K2CO3 and 80mL acetone were added to a 250mL three-necked flask,Add 0.05mol (12.07g) Bis(2-ethylhexyl)amine dropwise under ice bath and react for 2.0h.After the reaction, place the reaction liquid in a separatory funnel,Extract with ether, wash with saturated brine, and dry with anhydrous magnesium sulfate,Filter, the filtrate is rotary evaporated to remove the solvent,Obtain 2-bis(2-ethylhexyl)amino-4,6-dichloro-1,3,5-triazine.
  • 93
  • [ 106-20-7 ]
  • [ 142-62-1 ]
  • bis-(2-ethylhexyl)ammonium hexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 24.84℃; for 24h; 3.2. Synthesis of PILs General procedure: The synthesis of PILs was carried out by using a one-step neutralization reaction andthe reaction is written as follows:(Rx)2NH + HOOC(RY) (Rx)2NH2+ -OOC(RY)RX is 2-ethylhexyl or bis-(2-ethylhexyl and RY is either pentyl, hexyl or heptyl. In thiswork, 2-ethylhexylamine and bis-(2-ethylhexyl)amine, abbreviated as [EHA] and [BEHA],respectively, were the cations while the acids with the variation of alkyl chain length frompentyl [C5], hexyl [C6] and heptyl [C7] were the anions of the PILs.In a specific procedure, a 1:1 mol ratio of acid was added to the base with continuousstirring at 250 rpm for 24 h at room temperature. The resulting product was dried undervacuum at 80 C for 6 h to remove any water traces and impurities that might be presentresulting from starting reagents as well as surrounding atmosphere. The PILs which werein liquid forms without noticeable solid crystal or precipitation after the purification stepwere kept in sealed containers until further analysis. The proton transfer reaction hadresulted in the formation of six PILs as tabulated in Table 5. Figure 8 depicts the reactionfor the synthesis of [EHA][C5].
  • 94
  • [ 111-14-8 ]
  • [ 106-20-7 ]
  • bis-(2-ethylhexyl)ammonium heptanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 24.84℃; for 24h; 3.2. Synthesis of PILs General procedure: The synthesis of PILs was carried out by using a one-step neutralization reaction andthe reaction is written as follows:(Rx)2NH + HOOC(RY) (Rx)2NH2+ -OOC(RY)RX is 2-ethylhexyl or bis-(2-ethylhexyl and RY is either pentyl, hexyl or heptyl. In thiswork, 2-ethylhexylamine and bis-(2-ethylhexyl)amine, abbreviated as [EHA] and [BEHA],respectively, were the cations while the acids with the variation of alkyl chain length frompentyl [C5], hexyl [C6] and heptyl [C7] were the anions of the PILs.In a specific procedure, a 1:1 mol ratio of acid was added to the base with continuousstirring at 250 rpm for 24 h at room temperature. The resulting product was dried undervacuum at 80 C for 6 h to remove any water traces and impurities that might be presentresulting from starting reagents as well as surrounding atmosphere. The PILs which werein liquid forms without noticeable solid crystal or precipitation after the purification stepwere kept in sealed containers until further analysis. The proton transfer reaction hadresulted in the formation of six PILs as tabulated in Table 5. Figure 8 depicts the reactionfor the synthesis of [EHA][C5].
  • 95
  • [ 106-20-7 ]
  • [ 109-52-4 ]
  • bis-(2-ethylhexyl)ammonium pentanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 24.84℃; for 24h; 3.2. Synthesis of PILs General procedure: The synthesis of PILs was carried out by using a one-step neutralization reaction andthe reaction is written as follows:(Rx)2NH + HOOC(RY) (Rx)2NH2+ -OOC(RY)RX is 2-ethylhexyl or bis-(2-ethylhexyl and RY is either pentyl, hexyl or heptyl. In thiswork, 2-ethylhexylamine and bis-(2-ethylhexyl)amine, abbreviated as [EHA] and [BEHA],respectively, were the cations while the acids with the variation of alkyl chain length frompentyl [C5], hexyl [C6] and heptyl [C7] were the anions of the PILs.In a specific procedure, a 1:1 mol ratio of acid was added to the base with continuousstirring at 250 rpm for 24 h at room temperature. The resulting product was dried undervacuum at 80 C for 6 h to remove any water traces and impurities that might be presentresulting from starting reagents as well as surrounding atmosphere. The PILs which werein liquid forms without noticeable solid crystal or precipitation after the purification stepwere kept in sealed containers until further analysis. The proton transfer reaction hadresulted in the formation of six PILs as tabulated in Table 5. Figure 8 depicts the reactionfor the synthesis of [EHA][C5].
  • 96
  • [ 106-20-7 ]
  • [ 116808-70-9 ]
  • N-allyl-2-ethyl-N-(2-ethylhexyl)hexan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With 4,4′-dibenzyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole; copper(II) bromide In toluene at 100℃; for 24h; Sealed tube; Inert atmosphere; N-Allylation of Amines 1 with 2; General Procedure General procedure: In a nitrogen-filled glovebox, a sealed tube was charged with 2 (75.2 mg, 0.2 mmol), CuBr (2.8 mg, 0.02 mmol), BOX-1 (6.4 mg, 0.02 mmol), 1 (0.6 mmol) or 5 (0.4 mmol), and toluene (2.0 mL) with vigorous stirring. The mixture was reacted at 60 °C or 80 °C for 20 h or 24 h. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc) to give the desired product 3 or 6.
  • 97
  • [ 106-20-7 ]
  • decenyl glutaric anhydride [ No CAS ]
  • C31H59NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene at 80℃; for 2h; 8 (1) N,N-dihydrocarbyl secondary amine (24.2 g, 0.10 mol) represented by formula II-8 was dissolved in toluene (20 mL) to obtain solution one;The decenyl glutaric anhydride compound (25.4 g, 0.10 mol) represented by formula III-8 was dissolved in toluene (30 mL) to obtain solution two;(2) Add solution 1 to solution 2, stir the solution, raise the temperature to 80°C, and maintain the reaction temperature for 2 h. After the reaction, concentrate in vacuo to remove toluene to obtain compound I-8.
  • 98
  • [ 106-20-7 ]
  • decenyl pimelic anhydride [ No CAS ]
  • C33H63NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene at 80℃; for 2h; 9 (1) N,N-dihydrocarbyl secondary amine represented by formula II-9 (24.2 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution one;The decenyl pimelic anhydride compound (28.2 g, 0.10 mol) represented by formula III-9 was dissolved in toluene (30 mL) to obtain solution two;(2) Add solution 1 to solution 2, stir the solution, raise the temperature to 80°C, and maintain at the reaction temperature for 2 h. After the reaction, concentrate in vacuo to remove toluene to obtain compound I-9.
  • 99
  • [ 106-20-7 ]
  • dodecenyl glutaric anhydride [ No CAS ]
  • C33H63NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene at 80℃; for 2h; 1 1) N,N-diisooctyl secondary amine (24.2 g, 0.10 mol) represented by formula II-1 was dissolved in toluene (20 mL) to obtain solution one;The dodecenyl glutaric anhydride compound (26.7 g, 0.10 mol) represented by formula III-1 was dissolved in toluene (30 mL) to obtain solution two;(2) Add solution 1 to solution 2, stir the solution, raise the temperature to 80°C, and maintain the reaction temperature for 2 h. After the reaction, concentrate in vacuo to remove the inert solvent to obtain compound I-1.
  • 100
  • [ 106-20-7 ]
  • C17H29ClO3 [ No CAS ]
  • C33H63NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 80℃; for 2h; 1 N,N-dihydrocarbyl secondary amine (24.2g, 0.10mol) represented by formula II-1 and carboxylic acid monoacid chloride compound (31.7g, 0.10mol) represented by formula III-1a were directly mixed to form a mixed solution,The mixed solution was stirred, and the temperature was raised to 80° C., and maintained at the reaction temperature for 2 h. After the reaction was completed, compound I-1 was obtained.
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