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CAS No. : | 638-45-9 | MDL No. : | MFCD00001102 |
Formula : | C6H13I | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ANOOTOPTCJRUPK-UHFFFAOYSA-N |
M.W : | 212.07 | Pubchem ID : | 12527 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | 1760 |
Hazard Statements: | H302-H315-H318-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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 |
---|---|---|
52% | With dicarbonylbis(triphenylphosphine)platinum(0); potassium carbonate In tetrahydrofuran for 10h; Ambient temperature; Irradiation; photo-, electro-, and thermal carbonylation of alkyl iodides in the presence of group 7 and 8-10 metal carbonyl catalysts; | |
52% | With dicarbonylbis(triphenylphosphine)platinum(0); potassium carbonate In tetrahydrofuran for 10h; Ambient temperature; Irradiation; | |
52% | With potassium carbonate In tetrahydrofuran for 10h; Ambient temperature; Irradiation; |
75 % Chromat. | With bis(triphenylphosphine)platinum(II) dichloride; potassium carbonate In 1,4-dioxane at 120℃; for 9h; var. catalysts, bases, temp., CO pressures, and MeOH conc.; alkoxycarbonylation of other organic iodides; | |
79 % Chromat. | With potassium carbonate In 1,4-dioxane at 120℃; for 9h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate In ethanol for 22h; Heating; | ||
Stage #1: 4-bromo-phenol With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 0.5h; Stage #2: 1-Iodohexane In N,N-dimethyl-formamide at 70℃; | Synthesis of 4-Alkoxy-1-bromobenzene used for the synthesis of 7 General procedure: A mixture of 4-bromophenol (50 mmol),DMF(70ml) and potassium carbonate (100 mmol)was stirred at 70C for 0.5 h. To the suspension was added alkyl iodide (50 mmol) andthe mixture was stirred at 70C overnight. Water (200 ml) was added and the mixturewas extracted with hexane. The organic extracts were washed with brine (50 ml), 1NNaOH solution (50 ml) and water (100 ml), dried over MgSO4, and evaporated to give4-alkoxy-1-bromobenzene (> 90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 18-crown-6 ether; potassium carbonate In acetone for 12h; Heating; | |
95% | With 18-crown-6 ether; potassium carbonate In tetrahydrofuran for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With silver tetrafluoroborate; In acetonitrile; at 65℃; for 17h; | The reaction of thioarabinitol 63 (610 mg, 1.45 mmol) with the iodide 58 (0.211 mL, 1.43 mmol) and AgBF4 (276 mg, 1.43 mmol) in dry CH3CN (14 mL) gave compound 71 as a colorless syrup (810 mg, 95%): [alpha]D +4.00 (c 0.8, MeOH); 1H NMR (CD3OD): delta 7.37-7.24 (m, 15H, Ar), 4.65 and 4.62 (2d, each 1H, Ja,b=11.7 Hz, CH2Ph), 4.64 (br s, 1H, H-2), 4.56 and 4.47 (2d, each 1H, Ja,b=11.6 Hz, CH2Ph), 4.54 and 4.50 (2d, each 1H, Ja,b=11.7 Hz, CH2Ph), 4.39 (br s, 1H, H-3), 4.13 (dd, 1H, J4,5a=5 Hz, J4,5b=11.0 Hz, H-4), 4.04 (d, 1H, J1a,1b=12.5 Hz, H-1a), 3.88 (dd, 1H, J5a,4=5 Hz, J5a,5b=10.5 Hz, H-5a), 3.67 (dd, 1H, J1b,1a=12.5 Hz, J1b,2=3 Hz, H-1b), 3.64 (dd, 1H, J5b,5a=10.5 Hz, J5b,4=11.0 Hz, H-5b), 3.41 (ddd, 1H, J1'a,1'b=12.5 Hz, J1'a,2'a=J1'a,2'b=8.0 Hz, H-1'a), 3.31(ddd, 1H, J1'b,1'a=12.5 Hz, J1'b,2'a=5.5 Hz, J1'b,2'b=8.5 Hz, H-1'b), 1.82-1.68 (m, 2H, H-2'), 1.43-1.40 (m, 2H, H-3'), 1.21-1.18 (m, 4H, H-4' and H-5'), 0.85 (dd, 3H, J6',5'a=J6',5'b=7.0 Hz, H-6'); 13C NMR (CD3OD): delta 138.5, 138.3, 138.0 (3Cipso), 129.8-129.2 (15CAr), 84.3 (C-3), 84.2 (C-2), 74.6, 73.6, 73.1 (3 CH2Ph), 68.2 (C-5), 67.7 (C-4), 47.9 (C-1), 46.7 (C-1'), 32.2, 23.4 (C-4' and C-5'), 28.8 (C-3'), 26.7 (C-2'), 14.3 (C-6'); MALDI-TOF MS: m/z 505.34 [M-BF4]+. Anal. Calcd for C32H41BF4O3S: C, 64.86; H, 6.97. Found: C, 64.78; H, 7.10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; | Step A: 2-Hexanethio-4-hydroxypyrimidine To a stirred suspension of 10 g of thiouracil in THF (100 mL) was added triethylamine (22 mL) and iodohexane (11.5 mL). The mixture was heated to and maintained at reflux for 3 h. The heating bath was removed and the mixture was stirred overnight. Iodohexane (2 mL) was added and the mixture was brought to and maintained at reflux for 8 h. The heating bath was removed and the mixture was stirred overnight. Iodohexane (2 mL) was added and the mixture was brought to and maintained at reflux for 3 h. The mixture was allowed to cool to room temperature and the THF was removed under reduced pressure. The residue was diluted with water and extracted 3* with ethyl acetate. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated. The product was recrystallized from hexanes giving 8.45 g of the title compound. 1H NMR (500 MHz, CDCl3): delta 7.78 (1H,d, J=7 Hz); 6.23 (1H, d, J=7 Hz); 3.20 (2H, t, J=7.5 Hz); 1.73 (2H, m); 1.44 (2H, m); 1.32 (4H, m); 0.90 (3H, t, J=7 Hz). | |
With triethylamine; In tetrahydrofuran; | Step A 2-Hexanethio-4-hydroxypyrimidine To a stirred suspension of 10 g of thiouracil in THF (100 mL) was added triethylamine (22 mL) and iodohexane (11.5 mL). The mixture was heated to and maintained at reflux for 3 h. The heating bath was removed and the mixture was stirred overnight. Iodohexane (2 mL) was added and the mixture was brought to and maintained at reflux for 8 h. The heating bath was removed and the mixture was stirred overnight. Iodohexane (2 mL) was added and the mixture was brought to and maintained at reflux for 3 h. The mixture was allowed to cool to room temperature and the THF was removed under reduced pressure. The residue was diluted with water and extracted 3* with ethyl acetate. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated. The product was recrystallized from hexanes giving 8.45 g of the title compound. 1H NMR (500 MHz, CDCl3): delta 7.78 (1H, d, J=7 Hz); 6.23 (1H, d, J=7 Hz); 3.20 (2H, t, J=7.5 Hz); 1.73 (2H, (2H, m); 1.32 (4H, m); 0.90 (3H, t, J=7 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.2% | With sodium hydroxide; In ethanol; ethyl acetate; | Example 28 Synthesis of alpha-(3-Ethoxy-4hexyloxyphenyl)-N-tert-butylnitrone A solution of 3-ethoxy-4-hydroxybenzaldehyde (13.28 g, 79.9 mmol) and sodium hydroxide (3.20 g, 79.9 mmol) in ethanol (120 mL) was refluxed for 30 min. To the refluxing solution was added 1-iodohexane (18.6 g, 87.9 mmol) in one portion and reflux was continued for 24 h. The solution was then cooled and the ethanol removed on a rotary evaporator. The residue was dissolved in ethyl acetate and this solution filtered and rotary evaporated. The resulting residue was reacted with N-tert-butylhydroxylamine (6.94 g) in 200 mL of benzene in the presence of p-toluenesulfonic acid (0.8 g) at refluxing temperature for 24 h. After evaporation, the residue obtained was purified by recrystallization from hexanes to give the title compound (11.02 g, 57.2% overall yield) as a solid, m.p. 35.5 C. Spectroscopic data were as follows: IR (KBr, cm-1): 2900 (CH), 1596.2 (C=N), 1361.1 (CH,), 1276.0 (C--O--C) and 1144.8 (N--O). 1 H NMR (CDCl3, 270 MHz): delta=8.38 (1H, d, J=1.7 Hz, phenyl H), 7.45 (1H, dd, J=8.5 & 1.7 Hz, phenyl H), 7.42 (1H, s, nitronyl H), 6.86 (1H, d, J=8.5 Hz, phenyl H), 4.13 (2H, quartet, J=7.0 Hz, CH2), 4.02 (2H, t, J=6.8 Hz, CH2), 1.82 (2H, m, CH2), 1.65 (2H, m, CH2), 1.58 (9H, s, 3 CH3), 1.42 (3H, t, J=7.0 Hz, CH3), 1.31 (4H, m, 2 CH2) and 0.88 (3H, t, J=6.3 Hz, CH3). 13 C NMR (CDCl3, 67.9 MHz): delta=150.8, 148.6, 130.1, 124.4, 123.4, 113.4, 112.6, 70.0, 69.0, 64.4, 31.3, 28.7, 28.0, 25.3, 22.2, 14.4 and 13.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With potassium carbonate; In N,N-dimethyl-formamide; petrol; | EXAMPLE 6 1'Hexylspiro[indane-1,4'-piperidine] In the same way as that described in Example 1, step 5, the title compound was synthesised using spiro[indane-1,4'-piperidine] (0.4 g, 2.2 mmol), DMF (15 ml), potassium carbonate (0.33 g, 2.4 mmol) and iodohexane (0.62 g, 2.9 mmol). The crude residue was chromatographed in 1:1 petrol:ether to give 1'-hexylspiro[indane-1,4'-piperidine] (314 mg, 52%) as a pale yellow oil. The hydrochloride salt of the title amine (300 mg, 1.1 mmol) was prepared using ethereal hydrogen chloride, to give 1'-hexylspiro[indane-1,4'-piperidine]hydrochloride (177 mg, 52%) as white crystals, after recrystallisation from ethyl acetate/ethanol. m.p. 283-287 C. N.M.R. (D2 O) δ 0.89 (3H, t, J=7 Hz), 1.35 (6H, m), 1.79 (4H, m), 2.13 (4H, m), 298 (2H, t, J=7 Hz), 3.17 (4H, m), 3.60 (2H, m) 7.31 (4H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(a) Preparation of 3-tert-butyl-4-hexyloxybromobenzene Following the basic procedure of Example 46(a), by reacting 4.58 g (0.02 mol) of <strong>[10323-39-4]3-tert-butyl-4-hydroxybromobenzene</strong> with 3.3 ml (0.022 mol) of 1-iodohexane, 6 g (97%) of 3-tert-butyl-4-hexyloxybromobenzene were obtained in the form of a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate In acetone at 60℃; for 48h; | 161-1 In 10 ml of acetone was dissolved 510 mg (1.29 mmol) of commercial Nα-Boc-tryptophan benzyl ester, to which 1.12 ml of iodohexane was then added. Thereto was added 278 mg (0.853 mmol) of cesium carbonate, followed by stirring at 60°C for 2 days. After the end of reaction, the solvent was distilled off, followed by adding hexane and ethyl acetate to the residue before removing the insoluble matter by filtration. The solvent was distilled off, followed by purifying the residue using silica gel column chromatography (hexane/ethyl acetate) to provide 176 mg of the title compound as a colorless, viscous oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N-methyl-acetamide; | (1) A mixture of <strong>[4093-28-1]p-acetylaminosalicylic acid methyl ester</strong> (5.0 g), hexyl iodide (7.6 g), potassium carbonate (9.9 g), and dimethylformamide (20 ml) is stirred at 70° C. for 30 hours. The reaction mixture is poured into ice-water and extracted with diethyl ether. The organic layer is washed successively with aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated. The residue is chromatographed on silica gel with chloroform-methanol (20:1) to give 4-acetylamino-2-hexyloxybenzoic acid methyl ester (4.9 g) as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With C12H18ClCuN4O(1+)*ClO4(1-); caesium carbonate; In acetonitrile; at 80℃; for 24h;Inert atmosphere; | General procedure: In a flame-driedvessel, equipped with a magnetic stirrer, under argon atmosphere,were added 0.3 mL of anhydrous acetonitrile, the nucleophile (imidazoleor benzimidazole - 0.75 mmol, 1.5 eq.), the electrophile(alkyl or aryl iodide - 0.5 mmol, 1 eq.), the base (1 mmol, 2 eq.),and the copper catalyst (0.05 mmol - 10% loading). The reactionvessel was heated to 80 C and left under stirring for 24 h. Thereaction mixture was then allowed to cool to room temperature,diluted with dichloromethane (5 mL) and filtered through celite. The celitepad was further washed with dichloromethane(2 x 5 mL). The combined organic phases were washed with water(2 x 5 mL) and brine (2 x 5 mL). The organic solvents were thenremoved in vacuo to yield the crude product, which was purifiedby flash column chromatography on silica gel using a gradient mixtureof ethyl acetate/petroleum ether as eluent. The 1H and 13CNMR spectral data for all N-arylatedimidazoles and benzimidazolesare in full agreement with those reported to literature [57-61]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: benz<b>oxazole; carbon dioxide With (5-mesityl-2-(2-(2-(2-methoxyethoxy)ethoxy)phenyl)-2,3-dihydroimidazo[1,5-a]pyridin-3-yl)copper(I) chloride; potassium <i>tert</i>-butylate In tetrahydrofuran at 80℃; for 14h; Schlenk technique; Glovebox; Sealed tube; Stage #2: 1-Iodohexane In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube; | |
85% | Stage #1: benz<b>oxazole; carbon dioxide With 3-benzyl-1-(1-((2,6-diisopropylphenyl)imino)ethyl)-1H-imidazol-3-ium chloride; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere; Stage #2: 1-Iodohexane In N,N-dimethyl-formamide at 65℃; for 1h; Inert atmosphere; | 3 Synthesis of Benzoxazole-2-carboxylic acid hexyl ester by carboxylation reaction of benzoxazole with carbon dioxide In the reaction flask, Under argon, a catalyst (9.9 mg, 0.025 mmol, 5 mol%), potassium tert-butoxide (0.0672 g, 0.6 mmol) DMF (3.0 mL), benzoxazole (50.7 [mu] L, 0.5 mmol) The carbon dioxide gas was introduced and the reaction was stirred at 80 ° C for 18 hours under normal pressure. After cooling to 65 ° C, 1-iodohexane (222 μl, 1.5 mmol) was added, The reaction was stirred at 65 ° C for 1 hour. Cooled to room temperature, the reaction was terminated with deionized water, The reaction product was extracted with ethyl acetate and purified by column chromatography (Using a mixed solvent of ethyl acetate / petroleum ether in a volume ratio of 1:10 as a developing solvent) The yield was 85%. |
80% | Stage #1: benz<b>oxazole; carbon dioxide With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium <i>tert</i>-butylate In tetrahydrofuran at 80℃; for 14h; Inert atmosphere; Stage #2: 1-Iodohexane In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium hydroxide; In acetonitrile; for 24h;Reflux; | c, 2.6 mmol of 1, 14.5 mmol KOH and 2 mL of 1-iodo-n-hexane were dissolved in 30 mL of acetonitrile, refluxed for 24 hours, the solvent was removed to obtain a brown oil, dissolve with chloroform, and extracted and washed with distilled water 9 to 10 times. The filtrate was removed and the obtained brown solution was concentrated to 3 to 5 mL, and subjected to column chromatography with 100 to 200 mesh silica gel as the stationary phase and ethyl acetate as the eluent, Rf of the product was 0.7 to 0.8, to obtain dibenzimidazole phenyl complex 2 (yellow-white solid, yield 93%). |
89% | With potassium hydroxide; In acetonitrile; for 24h;Reflux; | c. Add 2.56 mmol of 1,14.3 mmol KOH and 2 mL of 1-iodo-n-hexane were dissolved in 30 mL of acetonitrile and refluxed for 24 hours. The solvent was removed to obtain a brown oil, which was dissolved in chloroform. Distilled water was extracted and washed 9-10 times, and the filtrate was taken to obtain a brown solution. Concentrated to 3 ~ 5mL, using 100 ~ 200 mesh silica gel as stationary phase, ethyl acetate was used as the eluent for column chromatography. The Rf of the product was 0.7 to 0.8. bisbenzimidazole phenyl complex 2 was obtained (yellow-white solid, yield 89%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: 10,15-dihydro-5H-5,10,15-triaza-diindeno[1,2-a;1',2'-c]fluorene With sodium hydride In N,N-dimethyl-formamide at 25℃; for 0.5h; Inert atmosphere; Stage #2: 1-Iodohexane In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; | |
75% | Stage #1: 10,15-dihydro-5H-5,10,15-triaza-diindeno[1,2-a;1',2'-c]fluorene With sodium hydride In N,N-dimethyl-formamide at 25℃; for 0.5h; Inert atmosphere; Stage #2: 1-Iodohexane In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; | |
75% | Stage #1: 10,15-dihydro-5H-5,10,15-triaza-diindeno[1,2-a;1',2'-c]fluorene With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: 1-Iodohexane In N,N-dimethyl-formamide for 2h; Inert atmosphere; Reflux; |
75% | Stage #1: 10,15-dihydro-5H-5,10,15-triaza-diindeno[1,2-a;1',2'-c]fluorene With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-Iodohexane In N,N-dimethyl-formamide at 160℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In acetonitrile; at 120℃; for 1h;Inert atmosphere; | 1,3-Bis(imidazol-1'-yl)benzene (1) (3.12 g, 14.7 mmol),1-iodohexane (45.0 mL, 305 mmol), and CH3CN (100 mL) werecombined in air, degassed, and heated at 120 C for 1 h. The reaction was cooled to room temperature, and concentrated under vacuum yielding a yellow solid. The solid was washedonto a frit with 1 : 1 CH3CN/Et2O (50 mL) and washed withadditional 1 : 1 CH3CN/Et2O (250 mL). The resulting whitesolid (7.64 g, 82 %) was dried under vacuum at 110 C overnight.dH (DMSO-d6) 10.01 (s, 2H), 8.45 (s, 2H), 8.38 (s, 1H), 8.15(s, 2H), 8.05-7.98 (m, 3H), 4.30 (t, 4H, J 7.3), 1.93 (m, 4H),1.315 (m, 12H), 0.87 (t, 6H, J 6.6). dC (DMSO-d6) 135.7, 135.6,131.9, 123.5, 122.6, 121.0, 115.7, 49.6, 30.5, 29.0, 25.1, 21.8,13.8; HRMS m/z 507.1965 [MI], calcd for C24H36IN4507.1979; 379.2847 [M2IH], calcd for C24H35N4379.2856. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 1-Iodohexane With triphenylphosphine In acetonitrile at 150℃; for 2h; Microwave irradiation; Inert atmosphere; Stage #2: benzyl bromide With potassium hexamethylsilazane In acetonitrile at 150℃; for 3h; Microwave irradiation; Inert atmosphere; Stage #3: With sodium hydroxide In acetonitrile at 100℃; for 1h; Microwave irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | In acetonitrile; for 16h;Darkness; Reflux; | A mixture of 1,4-di(4-pyridyl)benzene (0.82 g, 3.5 mmol) and 1-iodohexane (3.75 g, 17.7 mmol) in MeCN (30 mL) was heated under reflux in the dark for 16 h, cooled, filtered and washed with MeCN to give 4,4'-(1,4-phenylene)bis(1-hexylpyridin-1-ium) diiodide (1.10 g, 47percent) as a brown powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In acetonitrile for 16h; Darkness; Reflux; | 2 Example 2 A mixture of 2,6-di(4-pyridyl)naphthalene (0.60 g, 2.1 mmol) and 1-iodohexane (2.25 g, 10.6 mmol) in MeCN (30 mL) was heated under reflux in the dark for 16 h, cooled, filtered and washed with Et2O (10 mL) to give 4,4'-(naphthalene-2,6-diyl)bis(1-hexylpyridin-1-ium) diiodide (1.44 g, 96%) as a yellow powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 16 h / Darkness; Reflux 2: methanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a stirred solution of e-bromo-IH-pyrroloP^-clpyridine (800 mg, 4.06 mmol) in DMF (8 mL), NaH (60%), 243.6 mg, 6.09 mmol) was added at 0C. The reaction mixture was allowed to stir at RT for 45 min, then it was cooled to 0C and methyl iodide (384 mg, 2.706 mmol) was added to the mixture and stirred at RT for 3 h. The reaction mixture was quenched in ice water and extracted with EtOAc (2 x 50 mL), washed with brine (30 mL). The separated organic layer was dried over anhydrous Na2SO4, filtered and the filtrate was concentrated. The resultant crude compound was triturated with n-pentane to afford the title compound (500 mg, 58.6%) as a brown solid. LC-MS (method 1): Rt = 1.26 min; m/z = 210.95 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.9% | In acetone; at 56℃; for 120h;Inert atmosphere; | A mixture of <strong>[105-16-8]2-(diethylamino)ethyl methacrylate</strong> (DEAEMA, 27.789 g, 150.0 mmol), a slightexcess of 1-iodohexane (34.992 g, 165.0 mmol) and phenothiazine (0.6 g, 3.0 mmol) as inhibitor in15 mL acetonitrile was stirred under argon atmosphere at 60 C for 3 days and under exclusion ofUV irradiation. All volatile components were removed under reduced pressure. The precipitate waswashed with ethyl ether and dried under vacuum. The product was received as a white powder(57.18 g, 95.9% yield). M.p.: 95.7 C; 1H NMR (500 MHz, acetone-D6): delta (ppm) 0.91 (t, 3H, CH3); 1.39(m, 6H, CH2); 1.49 (t, 6H, CH3); 1.92 (m, 2H, CH2); 2.00 (s, 3H, CH3); 3.62 (m, 2H, CH2); 3.75 (q, 4H,CH2); 4.01 (m, 2H, CH2); 4.72 (s, 2H, CH2); 5.75 (s, 1H, CH2); 6.15 (s, 1H, CH2); 13C NMR (125 MHz,acetone-D6): delta (ppm) 7.4 (CH3); 13.3 (CH3); 17.5 (CH3); 21.7 (CH2); 22.2 (CH2); 25.8 (CH2); 31.1 (CH2);54.4 (CH2); 56.0 (CH2); 57.9 (CH2); 58.4 (CH2); 126.0 (CH2); 135.8 (C); 166.0 (C=O); IR (cm-1): 2954 nu(C-H); 1721 nu(C=O); 1640 nu(C=C); 1456 deltaas(CH2); 1403 deltas(CH3); 1296 nu(C-O); 1157 nu(C-O); 1060delta(CH2); 1011 delta(CH2); 936 delta(C-H); 808 delta(CH2); Elemental analysis calcd (%) for C16H32INO2: C, 48.37;H, 8.12; N, 3.53. Found (%): C, 48.43; H, 8.13; N, 3.50. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | 5-[4-aminophenyl] 1,3,4-oxadiazole-2-thiol (III) (0.5 g, 0.0026 mol) and potassiumhydroxide (0.15g, 0.0026 mol) dissolved in absolute ethanol and heated to reflux for30 min, after addition of iodohexane (0.38 ml, 0.0026 mol) the mixture was heated underreflux for three hours, the solvent was removed using rotary evaporator, an orange precipitatewas obtained by adding a few drops of cold distilled water to the solutionrecovered after evaporation. Yield 83%, mp 98C. IR, mmax/cm: 2965, 2865 (C-H aliphatic), 1114.6 (C-O, oxadiazole). 1-H NMR(DMSO-d6), 0.91 (3 H, t, H-12), 1.32-1.35 (2 H, m, H-11), 1.61 (2H, quint, H-10), 3.45 (2H,t, H-7), 6.01 (2 H, s, H-1’), 6.78-6.81 (2 H, d, H-2), 7.64-7.69 (2 H, d, H-3). 13-CNMR (DMSO-d6), 110.25 (1C, C-4), 113.86 (2C, C-2), 128.56 (2C, C-3), 152.79 (1C, C-1), 160.91 (1C, C-6), 166.57 (1C, C-5), 15.2 (1C, C-12), 25.41 (1C, C-11), 30.76 (1C,C-10), 27.89 (1C, C-9), 32.15 (1C, C-8), 35.26 (1C-C7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 52% 2: 32% | With caesium carbonate In acetonitrile at 82℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With nickel(II) bromide dimethoxyethane; lithium tert-butoxide; trimethylphosphane In 2-methyltetrahydrofuran at 60℃; for 24h; Schlenk technique; Inert atmosphere; | |
52% | With nickel(II) bromide dimethoxyethane; lithium tert-butoxide; trimethylphosphane In 2-methyltetrahydrofuran at 60℃; for 24h; Schlenk technique; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 47% 2: 9% | With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; for 16h; Inert atmosphere; | Dimethyl (4R,5R)-4-hexyl-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (33c)and dimethyl (4RS,5RS)-4,5-dihexyl-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (34c) A solution of LDA (prepared from iPr2NH (2.00 mL, 14.3 mmol) and n-BuLi (6.20mL, 1.6 M in hexanes, 9.92 mmol) in THF (50 mL) at -78 C) was added dropwiseover 4 h to a mixture of dimethyl (R,R)-tartrate acetonide (7) (1.40 mL, 7.62 mmol)and 1-iodohexane (1.00 mL, 6.78 mmol) in THF (50 mL) and HMPA (10 mL) at -78C. After 12 h, sat. aq NH4Cl (50 mL) was added, the organic layer was separated,and the aq layer was extracted with Et2O (3 × 100 mL). The combined organic layerswere dried (MgSO4) and concentrated under reduced pressure. Purification of theresidue by column chromatography (10% Et2O in petrol) gave monohexylatedtartrate 33c (967 mg, 47%) as a yellow oil; Rf 0.14 (10% Et2O in petrol); [α]D23 -27.5(c 1.0, CHCl3) ; max/cm-1(neat) 2956 s, 2859 s, 1761 s, 1438 m, 1374 m, 1209 s,1105 s, 995 m, 864 m; H(400 MHz, CDCl3) 4.93 (1H, s, CHCO2Me), 3.81 (3H, s,CO2Me), 3.80 (3H, s, CO2Me), 1.82-1.73 (1H, m, (CO2Me)CCHH), 1.67-1.62 (1H,m, (CO2Me)CCHH), 1.60 (3H, s, one of C(CH3)2), 1.41 (3H, s, one of C(CH3)2), 1.29-1.17 (8H, m, CH2CH2CH2CH2CH2CH3), 0.86 (3H, t, J 7, CH2CH3); C(100 MHz,CDCl3) 172.8 (CO2Me), 169.2 (CO2Me), 112.7 (C(CH3)2), 86.2 ((CO2Me)CCH2), 80.1(CHCO2Me), 52.9 (CO2Me), 52.4 (CO2Me), 34.4 ((CO2Me)CCH2), 31.7 (CH2), 29.5(CH2), 27.8 and 26.2 (C(CH3)2), 23.9 (CH2), 22.6 (CH2), 14.1 (CH2CH3); HRMS m/z(M+H+) found: 303.1803, C15H27O6 requires 303.1802.Also isolated was trans-dihexylated tartrate 34c (236 mg, 9%) as a yellow oil; Rf 0.47(10% Et2O in petrol); max/cm-1(neat) 2932 s, 2862 s, 1756 s, 1658 s, 1459 s, 1380 s,1321 s, 1242 s, 1143 s, 1058 s, 910 s, 859 s; H(400 MHz, CDCl3) 3.75 (6H, s, 2 CO2Me), 1.88 (1H, ddd, J 13, 12 and 4.5, (CO2Me)CCHH), 1.62-1.41 (10H, m, 2 (CO2Me)CCHH, CH2 and C(CH3)2), 1.29-1.13 (12H, m, 5 CH2 and 2 CHH),1.07-0.94 (2H, m, 2 CHH), 0.81 (6H, t, J 7, 2 CH2CH3); C(100 MHz, CDCl3)171.0 (2 x CO2Me), 112.0(C(CH3)2), 90.1 (2 x (CO2Me)CCH2), 52.4 (2 x CO2Me),35.5 ((CO2Me)CCH2), 31.6 (2 x CH2), 29.3 (C(CH3)2), 29.1 (2 x CH2), 24.0 (2 x CH2),22.5 (2 x CH2), 14.0 (2 x CH2CH3); HRMS m/z (M+H+) found: 387.2741, C21H39O6requires 387.2741. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.9 g | With sodium hydride; In N,N-dimethyl-formamide; at 20℃; | Add raw materials <strong>[143468-13-7]6-bromo-7-azaindole</strong> (3.0 g, 15.24 mmol), 1-iodohexane (3.60 g, 16.77 mmol), and sodium hydride to the two-necked flasks. (0.74g, 18.3mmol) and solvent N, N-dimethylformamide (10mL), react overnight at room temperature, directly spin the solvent, add water, extract with dichloromethane, collect the organic layer, dry, spin the solvent, Then pass the column to get 3.9g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In N,N-dimethyl-formamide; for 12h; | Add <strong>[143468-13-7]6-bromo-7-azaindole</strong> (15mmol), 1-iodohexane (1.1 times), sodium hydride (1.2 times) and N, N-dimethylformamide (15mL) to the reaction flask ,<strong>[143468-13-7]6-Bromo-7-azaindole</strong> sodium hydride needs to be added slowly in batches, react for 12 hours, add water, extract with dichloromethane, collect the organic phase, dry, remove the solvent, and finally pass through the column to obtain intermediate 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With nickel(II) iodide; samarium diiodide In tetrahydrofuran at 20℃; Glovebox; Inert atmosphere; |
Tags: 638-45-9 synthesis path| 638-45-9 SDS| 638-45-9 COA| 638-45-9 purity| 638-45-9 application| 638-45-9 NMR| 638-45-9 COA| 638-45-9 structure
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Code | Phrase |
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P370 + P376 | In case of fire: Stop leak if safe to Do so. |
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P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
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Disposal | |
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
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H260 | In contact with water releases flammable gases which may ignite spontaneously |
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Health hazards | |
Code | Phrase |
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H311 | Toxic in contact with skin |
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H316 | Causes mild skin irritation |
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H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
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H335 | May cause respiratory irritation |
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H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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