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Structure of 1071-93-8 * Storage: {[proInfo.prStorage]}
* 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.
With hydrazine hydrate In ethanol at 75℃; for 5 h;
General procedure: 7.6 g (100.0 mmol) of solid hydrazine (H3N + NHCO2-) and adipic acid (7.3 g, 50.0 mmol) were mixed in a mortar without a solvent for 10 minutes and stirred at 100 ° C for 5 hours. To confirm the structure and composition of the product produced in this process and analyzed using 400 MHz NMR (nuclear magnetic resonance) and elemental analysis) .As a result of the analysis, the product was adipohydrazide (C6H14N4O2), the conversion rate was 96percent or more, and the yield was 95percent or more. Yield (8.27 g, 96percent or more); The product was obtained in the same manner as in Example 1 except that 10 g of decane was used as a solvent and stirred at 110 DEG C for 12 hours and filtration and separation were carried out. The filtration and separation processes were carried out according to a known method. As a result of analysis on the product, the product was adipohydrazide (C6H14N4O2), the conversion was 97percent, and the yield was 93percent. 5.0 g (100.0 mmol) of hydrazine hydrate was used instead of the solid hydrazine and 10.12 g (100.0 mmol) of diethyl adipate was used instead of adipic acid.The product was obtained in the same manner as in Example 3 except that 10 g of ethanol was used as a solvent and the mixture was stirred at 75°C for 5 hours. As a result of analysis of the product, the product was adipohydrazide (C6H14N4O2), the conversion was 89percent, and the yield was 83percent.
Reference：
[1] Patent: KR2015/88523, 2015, A, . Location in patent: Paragraph 0128; 0137; 0148-0149
[2] Organic Syntheses, 1956, vol. 36, p. 72,Note 7
[3] Justus Liebigs Annalen der Chemie, 1929, vol. 475, p. 122
[4] Journal fuer Praktische Chemie (Leipzig), 1915, vol. <2> 91, p. 23
[5] Journal fuer Praktische Chemie (Leipzig), 1981, vol. 323, # 3, p. 360 - 366
[6] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1988, vol. 27, # 3, p. 225 - 230
[7] Russian Journal of Applied Chemistry, 2001, vol. 74, # 8, p. 1348 - 1352
[8] Journal of Coordination Chemistry, 2011, vol. 64, # 2, p. 300 - 313
[9] Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2012, vol. 74, # 1-4, p. 257 - 263
[10] Journal of Molecular Structure, 2015, vol. 1092, p. 122 - 129
2
[ 627-93-0 ]
[ 1071-93-8 ]
Yield
Reaction Conditions
Operation in experiment
99.2%
Stage #1: at 50 - 120℃; Stage #2: at 125℃; for 3 h;
2.1 g (0.15 mol) of dimethyl adipate was added to a four-necked flask equipped with a stir bar, a thermometer and a separatory funnel, and then 50.4 g (0.45 mol) of acetone and nitrogen were added thereto, and the mixture was heated to 50 ° C and stirred at a constant speed. Until the two are completely miscible,The mixture was obtained; the mixture was further heated. When the temperature of the mixture reached 120 ° C, 16.2 g (0.9 mol) of water was slowly added from the separatory funnel to the mixture at a rate of 25-30 seconds per drop. 18.5g of catalyst D072 macroporous strong acid styrene cation exchange resin was added to ensure the temperature of the system was reacted at 125 ° C for about 3 h until the dimethyl adipate was completely reacted to obtain the reaction product adipic acid dihydrazide; The complete acetone and nitrogen are distilled out.The solid in the flask is subjected to crystallization treatment, and the temperature of the system is lowered to about 25 ° C, and the solid is washed with anhydrous ethanol, and washed 3-5 times.It was dried in a vacuum oven at 60 ° C for 5 h to obtain 25.9 g of a white solid.That is, the target product adipic acid dihydrazide, the yield is 99.2percent,The purity was determined by HPLC to be 99.5percent.
83%
With hydrazine hydrate In isopropyl alcohol at 20℃; for 16 h; Heating
The adipic acid dimethyl ester (7.5 g; 0.04 mol) was added dropwise to a solution of isopropyl alcohol (20 ml) and hydrazine hydrate (5 ml), heated to a boiling point, then the reaction mixture was allowed to stand for 16 hours at +20° C. The precipitate was separated, washed with isopropyl alcohol, and dried. The amount of the resulting adipic acid dihydrazide with a melting point of 182-182.5° C. was 6.2 (83percent).
81%
With hydrazine hydrate In methanol at 60℃; for 5 h;
General procedure: 7.6 g (100.0 mmol) of solid hydrazine (H3N + NHCO2-) and adipic acid (7.3 g, 50.0 mmol) were mixed in a mortar without a solvent for 10 minutes and stirred at 100 ° C for 5 hours. To confirm the structure and composition of the product produced in this process and analyzed using 400 MHz NMR (nuclear magnetic resonance) and elemental analysis) .As a result of the analysis, the product was adipohydrazide (C6H14N4O2), the conversion rate was 96percent or more, and the yield was 95percent or more. Yield (8.27 g, 96percent or more); The product was obtained in the same manner as in Example 1 except that 10 g of decane was used as a solvent and stirred at 110 DEG C for 12 hours and filtration and separation were carried out. The filtration and separation processes were carried out according to a known method. As a result of analysis on the product, the product was adipohydrazide (C6H14N4O2), the conversion was 97percent, and the yield was 93percent. 5.0 g (100.0 mmol) of hydrazine hydrate was used instead of the solid hydrazine8.71 g (100.0 mmol) of dimethyl adipate was used instead of adipic acid. The product was obtained by following the same procedure as in Example 3, except that 10 g of methanol was used as a solvent and the mixture was stirred at 60 ° C for 5 hours. As a result of analysis of the product, the conversion was 87percent and the yield was 81percent.
4.6 g
With hydrazine In methanol at 50℃; for 1 h;
To a solution of dimethyl adipate (28.7 mmol, 5.0 g, 4.7 mL, 1.0 equiv.) in 20 mL of MeOH was added anhydrous hydrazine (229.6 mmol, 7.36 g, 7.51 mL, 8.0 equiv.) and the mixture heated to 50°C, giving a white precipitate. The mixture was heated for one hour and then allowed to cool to room temperature. The white solid was collected by filtration and washed with additional MeOH then dried under high vacuum giving 4.6 g of adipohydrizide. 1HNMR (300 MHz, DMSO-d6) δ 8.91 (s, 2H), 4.14 (s, 4H), 2.00 (br s, 4H), 1.46 (br s, 4H).
Reference：
[1] Patent: CN108191708, 2018, A, . Location in patent: Paragraph 0020-0033
[2] Patent: US2016/31858, 2016, A1, . Location in patent: Paragraph 0147
[3] Patent: KR2015/88523, 2015, A, . Location in patent: Paragraph 0128; 0137; 0150-0151
[4] Synthesis, 1993, # 3, p. 287 - 289
[5] J. Gen. Chem. USSR (Engl. Transl.), 1964, vol. 34, p. 341 - 344[6] Zhurnal Obshchei Khimii, 1964, vol. 34, p. 343 - 347
[7] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997, vol. 36, # 8, p. 687 - 690
[8] Patent: WO2013/78123, 2013, A1, . Location in patent: Page/Page column 85
[9] Journal of Materials Chemistry B, 2016, vol. 4, # 5, p. 852 - 858
3
[ 124-04-9 ]
[ 1071-93-8 ]
Yield
Reaction Conditions
Operation in experiment
96%
With carbazic acid In neat (no solvent) at 100℃; for 5 h; Green chemistry
7.6 g (100.0 mmol) of solid hydrazine (H3N + NHCO2-) and adipic acid (7.3 g, 50.0 mmol) were mixed in a mortar without a solvent for 10 minutes and stirred at 100 ° C for 5 hours. To confirm the structure and composition of the product produced in this process and analyzed using 400 MHz NMR (nuclear magnetic resonance) and elemental analysis) .As a result of the analysis, the product was adipohydrazide (C6H14N4O2), the conversion rate was 96percent or more, and the yield was 95percent or more. Yield (8.27 g, 96percent or more);
Reference：
[1] Patent: KR2015/88523, 2015, A, . Location in patent: Paragraph 0127-0130
[2] Patent: US2016/31858, 2016, A1,
4
[ 124-04-9 ]
[ 10195-79-6 ]
[ 1071-93-8 ]
Yield
Reaction Conditions
Operation in experiment
96%
at 100℃; for 5 h;
5.4 g (50.0 mmol) of anhydrous hydrazinium hydrazinecarboxylate and 7.3 g (50.0 mmol) of adipic acid were mixed in a mortar without a solvent for 10 minutes and stirred at 100 ° C for 5 hours.In order to confirm the structure and composition of the product formed in this process, 400 MHz NMR (Nuclear Magnetic Resonance) and elemental analysis were used.
With hydrazine hydrate; In ethanol; at 75℃; for 5h;
General procedure: 7.6 g (100.0 mmol) of solid hydrazine (H3N + NHCO2-) and adipic acid (7.3 g, 50.0 mmol) were mixed in a mortar without a solvent for 10 minutes and stirred at 100 C for 5 hours. To confirm the structure and composition of the product produced in this process and analyzed using 400 MHz NMR (nuclear magnetic resonance) and elemental analysis) .As a result of the analysis, the product was adipohydrazide (C6H14N4O2), the conversion rate was 96% or more, and the yield was 95% or more. Yield (8.27 g, 96% or more); The product was obtained in the same manner as in Example 1 except that 10 g of decane was used as a solvent and stirred at 110 DEG C for 12 hours and filtration and separation were carried out. The filtration and separation processes were carried out according to a known method. As a result of analysis on the product, the product was adipohydrazide (C6H14N4O2), the conversion was 97%, and the yield was 93%. 5.0 g (100.0 mmol) of hydrazine hydrate was used instead of the solid hydrazine and 10.12 g (100.0 mmol) of <strong>[141-28-6]diethyl adipate</strong> was used instead of adipic acid.The product was obtained in the same manner as in Example 3 except that 10 g of ethanol was used as a solvent and the mixture was stirred at 75C for 5 hours. As a result of analysis of the product, the product was adipohydrazide (C6H14N4O2), the conversion was 89%, and the yield was 83%.
With hydrazine hydrate; In ethanol; for 0.5h;Reflux;
Preparation of bis(2-hydroxy-1-naphthaldehyde)adipoyldihydrazone Adipoyldihydrazide was prepared by reacting <strong>[141-28-6]diethyl adipate</strong> (1.00 g) with hydrazine hydrate (0.55 g) in 1:2 molar ratio in 20 mL ethanol under reflux for 30 mins. The product was recrystallized from dilute ethanol.
2.1 g (0.15 mol) of <strong>[627-93-0]dimethyl adipate</strong> was added to a four-necked flask equipped with a stir bar, a thermometer and a separatory funnel, and then 50.4 g (0.45 mol) of acetone and nitrogen were added thereto, and the mixture was heated to 50 C and stirred at a constant speed. Until the two are completely miscible,The mixture was obtained; the mixture was further heated. When the temperature of the mixture reached 120 C, 16.2 g (0.9 mol) of water was slowly added from the separatory funnel to the mixture at a rate of 25-30 seconds per drop. 18.5g of catalyst D072 macroporous strong acid styrene cation exchange resin was added to ensure the temperature of the system was reacted at 125 C for about 3 h until the <strong>[627-93-0]dimethyl adipate</strong> was completely reacted to obtain the reaction product adipic acid dihydrazide; The complete acetone and nitrogen are distilled out.The solid in the flask is subjected to crystallization treatment, and the temperature of the system is lowered to about 25 C, and the solid is washed with anhydrous ethanol, and washed 3-5 times.It was dried in a vacuum oven at 60 C for 5 h to obtain 25.9 g of a white solid.That is, the target product adipic acid dihydrazide, the yield is 99.2%,The purity was determined by HPLC to be 99.5%.
94%
With hydrazine hydrate; at 20℃; for 72h;
In one embodiment, hydrazine hydrate is used to convert <strong>[627-93-0]dimethyl adipate</strong> to ADH. In another embodiment, the composition of hydrazine hydrate is 95%. In another embodiment, 372ml of an 82% composition of hydrazine hydrate is mixed with 200ml of 0.006M <strong>[627-93-0]dimethyl adipate</strong> and stirred for 72 hours at room temperature resulting ADH (200g, 94%) to be used without further purification.
83%
With hydrazine hydrate; In isopropyl alcohol; at 20℃; for 16h;Heating;
The adipic acid dimethyl ester (7.5 g; 0.04 mol) was added dropwise to a solution of isopropyl alcohol (20 ml) and hydrazine hydrate (5 ml), heated to a boiling point, then the reaction mixture was allowed to stand for 16 hours at +20 C. The precipitate was separated, washed with isopropyl alcohol, and dried. The amount of the resulting adipic acid dihydrazide with a melting point of 182-182.5 C. was 6.2 (83%).
81%
With hydrazine hydrate; In methanol; at 60℃; for 5h;
General procedure: 7.6 g (100.0 mmol) of solid hydrazine (H3N + NHCO2-) and adipic acid (7.3 g, 50.0 mmol) were mixed in a mortar without a solvent for 10 minutes and stirred at 100 C for 5 hours. To confirm the structure and composition of the product produced in this process and analyzed using 400 MHz NMR (nuclear magnetic resonance) and elemental analysis) .As a result of the analysis, the product was adipohydrazide (C6H14N4O2), the conversion rate was 96% or more, and the yield was 95% or more. Yield (8.27 g, 96% or more); The product was obtained in the same manner as in Example 1 except that 10 g of decane was used as a solvent and stirred at 110 DEG C for 12 hours and filtration and separation were carried out. The filtration and separation processes were carried out according to a known method. As a result of analysis on the product, the product was adipohydrazide (C6H14N4O2), the conversion was 97%, and the yield was 93%. 5.0 g (100.0 mmol) of hydrazine hydrate was used instead of the solid hydrazine8.71 g (100.0 mmol) of <strong>[627-93-0]dimethyl adipate</strong> was used instead of adipic acid. The product was obtained by following the same procedure as in Example 3, except that 10 g of methanol was used as a solvent and the mixture was stirred at 60 C for 5 hours. As a result of analysis of the product, the conversion was 87% and the yield was 81%.
4.6 g
With hydrazine; In methanol; at 50℃; for 1h;
To a solution of <strong>[627-93-0]dimethyl adipate</strong> (28.7 mmol, 5.0 g, 4.7 mL, 1.0 equiv.) in 20 mL of MeOH was added anhydrous hydrazine (229.6 mmol, 7.36 g, 7.51 mL, 8.0 equiv.) and the mixture heated to 50C, giving a white precipitate. The mixture was heated for one hour and then allowed to cool to room temperature. The white solid was collected by filtration and washed with additional MeOH then dried under high vacuum giving 4.6 g of adipohydrizide. 1HNMR (300 MHz, DMSO-d6) delta 8.91 (s, 2H), 4.14 (s, 4H), 2.00 (br s, 4H), 1.46 (br s, 4H).
With hydrazine hydrate; In methanol; for 8h;Reflux;
(a) To methanolic solution of adipic acid (1.00 g, 6.66 mmol) a few drops of conc. sulphuricacid were added and the reaction mixture was refluxed for 24 h. In vacuoreduction of volume with mild heating was done to afford <strong>[627-93-0]dimethyl adipate</strong> as viscoustransparent oil. Further, <strong>[627-93-0]dimethyl adipate</strong> reacted with hydrazine hydrate (0.68 g,13.65 mmol) in methanolic solution and was refluxed for 8 h. White crystals wereobtained on cooling to room temperature that were isolated by filtration, washedwith diethyl ether and dried in a desiccator. 1H NMR (500 MHz, DMSO, ppm): delta = 8.90(s, 2H, -CONH), 4.16 (s, 4H, -NHNH2), 1.94 (s, 4H, CH2), 1.77 (d, 2H, CH2).
With hydrazine hydrate; In methanol; at 80℃; for 0.000555556h;
Dissolving <strong>[627-93-0]dimethyl adipate</strong> in methanol, Make a 1.5mol/L solution for use. 80% by mass of hydrazine hydrate is dissolved in methanol, A 3 mol/L solution was prepared for use. A methanol solution of <strong>[627-93-0]dimethyl adipate</strong> was injected into the microchannel reactor or the pipeline reactor through a metering pump at a flow rate of 50 ml/min. The hydrazine hydrated methanol solution was injected into the microchannel reactor or pipeline reactor through another metering pump at a flow rate of 63.1 ml/min. React at 80 C for 2 seconds, Flow out of the microchannel reactor or pipeline reactor, Collecting reaction materials, Obtaining a white crystalline product with a content of 99.9%, The monoterpene content is 0.01%. The reaction mother liquid methanol was filtered and applied.
3 2.3. Synthesis of bis(2-hydroxynaphthaldehyde)adipicdihydrazone (H4Lb)
A mixture of adipic dihydrazide (0.174 g, 1 mmol) and 2-hydroxynaphthaldehyde (0.430 g, 2.5 mmol) was refluxed in ethanol for 5 h. After this time the milky precipitate was filtered and washed with ethanol. Yield: 0.310 g (65%); m.p. 220 °C; IR (KBr, cm-1): ν(NH/OH), 3100-3200 br; ν(C=O), 1659; ν(C=N), 1615. 1H NMR (DMSO-d6): δ = 1.70 (t, br, 4H, CH2), 2.33 (t, br, 4H, CH2), 7.20 (d, 2H, H1, 3JHH = 8.7 Hz), 7.40 (t, 2H, H4, 3JHH = 7.6 Hz), 7.58 (t, 2H, H5, 3JHH = 7.7 Hz), 7.87 (m, 4H, H2, 3), 8.20 (d, 2H, H6, 3JHH = 8.6 Hz), 9.16 (s, 2H, HC=N), 11.75 (s, 2H, NH), 12.65 (s, 2H, OH).
61.53%
In ethanol at 50℃;
Preparation of bis(2-hydroxy-1-naphthaldehyde)adipoyldihydrazone
Bis(2-hydroxy-1-naphthaldehyde)adipoyldihydrazone (npahH4)was then prepared by reacting a solution of adipoyldihydrazide(1.00 g) in 20 mL of ethanol with 2-hydroxy-1-naphthaldehyde(2.18 g) in 1:2 molar ratio in ethanol over a hot plate at 50 C withconstant gentle stirring. The yellow precipitate obtained on coolingthe solution was thoroughly washed with ethanol and air dried(yield of 61.53%; m.p. > 300 C).
N'1,N'6-bis(3-(1-pyrrolyl)propanoyl)hexanedihydrazide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
Stage #1: N-(2-carboxyethyl)pyrrole With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 2h;
Stage #2: adipic acid dihydrazide In dimethyl sulfoxide
N,N'-bis-[2-(1H-imidazol-4-yl)ethyl]hexanediamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
Stage #1: adipic acid dihydrazide With hydrogenchloride; sodium nitrate In chloroform; water Cooling with ice;
Stage #2: histamine In chloroform; isopropyl alcohol at 4℃; for 24h;
7 Example 7 Bis-1,5-(Nβ-histaminyl)adipic acid; (N,N′-bis-[2-(1H-imidazol-4-yl)ethyl]hexanediamide) (Compound 12)
Sodium nitrate (1.8 g; 0.026 mol) was added portionwise under , 24.97. C16H24N6O2. Calculated, %: C, 57.81; H, 7.28; N, 25.28.stirring to a solution of the adipic acid dihydrazide (2.2 g; 0.013 mol) in a mixture of ice (30 g) with hydrochloric acid (3 ml) and cooled chloroform (15 ml). The chloroform layer was separated, washed with water (10 ml), and cooled to +4° C., then isopropanol (8 ml) was added to the cooled histamine solution (3 g; 0.027 mol). The completeness of the reaction was checked by a TLC or electrophoresis method. The reaction mixture was allowed to stand for 24 hours at +4° C., and the residue was separated, washed with isopropyl alcohol, recrystallized from water, and dried. The yield was 2.8 g (65%). Rf 0.48 (1). E+45 mm. M.p. 184-186° C. [M+H]+ 332.92. 1H-NMR (D2O): δ, m.d.: 1.37-1.41 (m, 4H, β-CH2-Adip), 2.11-2.15 (m, 4H, α-CH2-Adip), 2.74-2.78 (t, 4H, β-CH2-HA), 3.40-3.44 (t, 4H, α-CH2-HA), 6.88 (s, 2H, 5-CH-Im), 7.63 (s, 2H, 2-CH-Im). Fourier-IR spectrum (in a KBr table, ν, cm-1): 1646 (ν C═O amide I), 1581 (δ NH amide II), 1425 (-CH2-CO-). Found, %: C, 57.45; H, 7.15; N, 24.97. C16H24N6O2. Calculated, %: C, 57.81; H, 7.28; N, 25.28.
With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene; acetone at 140℃; for 6h;
1.1 1) Preparation of adipic dihydrazone:
84.9 g (0.488 mol) of adipic dihydrazide, 158 · 2 g (1.0 mol) of triacetonamine was completely dissolved in 200 mL of acetone, 2.95 g (0.049 mol) of acetic acid was added in one portion, the resulting solution was diluted with 1000 mL of dimethylbenzene, it was transferred to a 2L glass reactor equipped with a water-oil separator, and uniformly mixed, and then heated to 140 ° C for 6 h. The reaction solution was cooled to 0 ° C with chilled water and allowed to stand for 2 h, and a pale yellow solid precipitated in the system, after filtration, the solid was washed twice with cold ethanol (200 mL), after drying, 203.3 g of a pale yellow solid was obtained, the melting point of the test was 83-84 ° C, and the calculated yield was 93%, which satisfies the hydrogenation requirement.
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