Structure of 69506-85-0
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CAS No. : | 69506-85-0 |
Formula : | C9H12N4 |
M.W : | 176.22 |
SMILES Code : | N1(CCCN2C=CN=C2)C=CN=C1 |
MDL No. : | MFCD11110663 |
InChI Key : | ISXPITWIJWSEKJ-UHFFFAOYSA-N |
Pubchem ID : | 15028898 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | General procedure: The general procedure for the Nalkylation of heterocycles was as follows.22 Heterocycle (1 mmol) wasdissolved in 5 ml anhydrous DMF. Then complex(0.05 mmol) and K2CO3 was added to the solution atroom temperature. Shortly afterwards (20 min),1,3-dibromopropane (1 mmol) was added in portions to the reaction mixture. The reaction was stirred at room temperature. The inorganic salt was removed byfiltration and rinsed twice with dichloromethane. The solution was poured into water and extracted withdichloromethane (2 x 25 ml). The combined organiclayers were washed with brine, dried over anhydroussodium sulphate, filtered, and concentrated in vacuoresulting in the formation of the product in 92 % yieldwith coupling ratio 1:1 and product yield 78 % withcoupling ratio 2:1. Nalkylation of heterocycles with1,3-dibromopropane having 1:1 coupling proportion(Scheme-2) is easier than 2:1 coupling proportion(Scheme-3). | |
52% | 1,3-Di(imidazolyl-1)propane: Imidazole (13.6 g,0.2 mol) was dissolved in 50 mL of acetonitrile, and22.4 g (0.2 mol) of potassium tert-butoxide was addedportionwise (the reaction is exothermic) with stirringon a magnetic stirrer. The resulting mixture was stirredfor 1 h, and the solvent was then distilled off in vacuum(to remove tert-butanol). Acetonitrile (70 mL) wasadded to the dry residue, and 20.4 g (0.1 mol) of1,3-dibromopropane dissolved in 20 mL of acetonitrilewas added dropwise over 1 h under stirring. Theprecipitate of KBr was filtered off the next day, the filtratewas evaporated in vacuum, and the residue wasdistilled in vacuum. The product was distilled at 198-200C/<1 mmHg as a pale-yellow viscous liquid thatcrystallizes later, m.p. 45C. The yield was 9.1 g (52%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With hydrogenchloride; In water; at 25 - 160℃; for 96h;pH 4.0;Autoclave; | A mixture of H3PMo12O40·13H2O (0.6178g, 0.3mmol), bpi (0.035g, 0.2mmol) and H2O (10ml) was stirred for 30min in air until it was homogeneous. When the pH value of the mixture was adjusted to 4 with 1M HCl, the solution was transferred and sealed in a 30-ml Teflon-lined stainless steel autoclave, which was heated at 160C under autogenous pressure for 4days. The dark blue block crystals were isolated and collected by filtration, washed thoroughly with distilled water, and dried at room temperature (60% yield based on Mo). Anal. Calc. C18H27N8O40PMo12 (4295.10): C, 4.99 (Calc. 5.03); H, 0.69 (0.63); N, 2.69 (2.61); P, 0.74(0.72); Mo, 26.79 (26.82) wt.% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With hydrogenchloride; In water; at 25 - 170℃; for 96h;pH 4.0;Autoclave; | A mixture of H3PMo12O40·13H2O (0.6178g, 0.3mmol), bpi (0.0175g, 0.1mmol), bbi (0.019g, 0.1mmol) and H2O (10ml) was stirred for 30min in air until it was homogeneous. When the pH value of the mixture was adjusted to 4 with 1M HCl, the solution was transferred and sealed in a 30-ml Teflon-lined stainless steel autoclave, which was heated at 170C under autogenous pressure for 4days. The light blue sheet crystals were isolated and collected by filtration, washed thoroughly with distilled water, and dried at room temperature (63% yield based on Mo). Anal. Calc. C14H21N6O40PMo12 (2095.62): C, 7.99 (Calc. 8.02); H, 0.99 (1.00); N, 3.99 (4.01); P, 1.44 (1.48); Mo, 54.61 (54.97) wt.%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With potassium hydroxide; In water; at 139.84℃; for 72h;Autoclave; | The reaction condition is similar to those described in 1 except that 1,2-bie was replaced by 1,3-bip (17.6mg, 0.1mmol). Colorless block crystals of 2 were obtained. Yield: 19.6mg, 42percent (Based on Cd). Anal. Calc. for C18H18CdN4O4: C, 46.32; H, 3.89; N, 12.00. Found: C, 46.28; H, 3.93; N, 11.96percent. IR (cm?1): 3484 m, 3118 m, 1615 m, 1546 s, 1370 s, 1090 s, 780 s, 730 s, 659 s. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium hydroxide; In water; at 110℃; for 72h; | A mixture of Cd(OAc)2.2H2O (0.2 mmol, 60 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.20 mmol, 35.2 mg), NaOH (0.2 mmol, 8 mg) and 1.4-bdc (0.20 mmol, 38.0 mg) in distilled water (4 mL) was placed in a vial, heated to 110C for 3 d, and then cooled to room temperature over 24 h. Colorless block crystals of 1 were collected. Yield: 82% based on cadmium. Elemental analysis (%): calcd for C17H16N4O4Cd (Mr = 452.75): C 45.06, H 3.53, N 12.37; found: C 45.36, H 4.12, N12.81. IR (cm-1): 3417 (w), 3120 (m), 2945 (m), 2884 (w), 1610(s), 1565 (s), 1513 (s), 1379 (s), 1279 (m), 1027 (m), and 833 (m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydroxide; In water; at 110℃; for 72h; | General procedure: A mixture of Cd(OAc)2.2H2O (0.2 mmol, 60 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.20 mmol, 35.2 mg), NaOH (0.2 mmol, 8 mg) and 1.4-bdc (0.20 mmol, 38.0 mg) in distilled water (4 mL) was placed in a vial, heated to 110C for 3 d, and then cooled to room temperature over 24 h. Colorless block crystals of 1 were collected. Yield: 82% based on cadmium. Elemental analysis (%): calcd for C17H16N4O4Cd (Mr = 452.75): C 45.06, H 3.53, N 12.37; found: C 45.36, H 4.12, N12.81. IR (cm-1): 3417 (w), 3120 (m), 2945 (m), 2884 (w), 1610(s), 1565 (s), 1513 (s), 1379 (s), 1279 (m), 1027 (m), and 833 (m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium hydroxide; at 110℃; for 72h; | A mixture of Cd(OAc)2.2H2O (0.2 mmol, 60 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.20 mmol, 35.2 mg), NaOH (0.2 mmol, 8 mg) and 1.3-bdc (0.20 mmol, 38.0 mg) in distilled water (4 mL) was placed in a vial, heated to 110C for 3 d, and then cooled to room temperature over 24 h. Colorless block crystals of 3 were obtained. Yield: 76% based on cadmium. Elemental analysis (%): calcd for C17H18CdN4O5 (Mr = 470.75): C 43.33, H 3.82, N 11.89; found: C 43.28, H 3.77, N11.96. IR (cm-1): 3414 (bs), 3122 (w), 1601 (s), 1551 (s), 1435(w), 1232 (m), 1096 (m), 932 (w), 749 (s), and 622 (w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium hydroxide; at 110℃; for 72h; | General procedure: A mixture of Cd(OAc)2.2H2O (0.2 mmol, 60 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.20 mmol, 35.2 mg), NaOH (0.2 mmol, 8 mg) and 1.3-bdc (0.20 mmol, 38.0 mg) in distilled water (4 mL) was placed in a vial, heated to 110C for 3 d, and then cooled to room temperature over 24 h. Colorless block crystals of 3 were obtained. Yield: 76% based on cadmium. Elemental analysis (%): calcd for C17H18CdN4O5 (Mr = 470.75): C 43.33, H 3.82, N 11.89; found: C 43.28, H 3.77, N11.96. IR (cm-1): 3414 (bs), 3122 (w), 1601 (s), 1551 (s), 1435(w), 1232 (m), 1096 (m), 932 (w), 749 (s), and 622 (w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | at 120℃; for 72h;High pressure; Autoclave; | A mixture of 3,5-pdc (0.10 mmol,16.7 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.10 mmol, 17.6 mg) and Zn(NO3)2.6H2O (0.10 mmol, 30.8 mg) in distilled water (15 mL) was placed in a Teflon-lined stainless steel vessel, heated to 120 C for 3 days, and then cooled to room temperature over 24 h. Colourless block crystals of 1 were obtained. Yield 51%. Anal calcd for C16H19N5O6Zn (Mr = 442.72): C, 43.38; H, 4.29; N, 15.81; found: C, 43.24; H, 3.96; N, 15.90%. IR(cm-1): 3455 (s), 3125 (m),2934 (w), 1668 (s), 1627 (s), 1530 (m), 1353(s),1247 (w), 1103 (s), 946 (w), 835 (w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | at 120℃; for 72h;Autoclave; High pressure; | A mixture of 1,3-bdc (0.10 mmol,16.7 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.10 mmol, 17.6 mg) and Cu(NO3)2 (0.10 mmol,24.1 mg) in distilled water (15 mL) was placed in a Teflon-lined stainless steel vessel, heated to 120 C for 3 d, and then cooled to room temperature over 24 h. Blue block crystals of the title compound were collected. Yield 71%. Anal calcd for C17H18CuN4O5 (Mr = 421.88):C, 48.35; H, 4.26; N, 13.27; found: C, 48.61; H, 4.04; N, 13.40%. IR (cm-1): 3433 (s),3120 (s),2928 (m),1612 (s),1557 (m),1396(m),1352 (s),1235 (w), 1096 (m), 733 (m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In acetonitrile; at 75℃;Schlenk technique; Inert atmosphere; | General procedure: A mixture of the properly functionalised benzyl bromide (1 mmol) and <strong>[69506-85-0]1,3-di(1H-imidazol-1-yl)propane</strong> (0.5 mmol) in acetonitrile (15 mL) was left under stirring at 75 C for 16 h. Addition of diethyl ether (20 mL) to the reaction mixture affords the precipitation of the product. The obtained white solid was isolated, washed with diethyl ether (2 x 5 mL) and dried under vacuum. 1·2HBr: White solid, yield 62%. Anal Calcd for C39H58Br2N4O25H2O: C, 54.17; H, 7.93; N, 6.48%. Found: C, 54.44; H, 7.68; N, 6.60%. 1H NMR (CDCl3): δ=0.88 (m, 6H, CH3), 1.10-1.50 (m, 20H, CH2), 1.77 (m, 4H, OCH2CH2), 2.88 (m, 2H, CH2 propylene), 3.94 (m, 4H, OCH2), 4.72 (m, 4H, NCH2 propylene), 5.31 (s, 4H, NCH2Ar), 6.91 (d, 3J=8.5Hz, 4H, Ar-H), 6.96 (s, 2H, CH), 7.35 (d, 3J=8.5Hz, 4H, Ar-H), 8.05 (s, 2H, CH), 10.21 (s, 2H, NCHN). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In acetonitrile; at 75℃;Schlenk technique; Inert atmosphere; | General procedure: A mixture of the properly functionalised benzyl bromide (1 mmol) and <strong>[69506-85-0]1,3-di(1H-imidazol-1-yl)propane</strong> (0.5 mmol) in acetonitrile (15 mL) was left under stirring at 75 C for 16 h. Addition of diethyl ether (20 mL) to the reaction mixture affords the precipitation of the product. The obtained white solid was isolated, washed with diethyl ether (2 x 5 mL) and dried under vacuum. |