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CAS No. : | 3839-35-8 | MDL No. : | MFCD00059439 |
Formula : | C13H20O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IVQOVYWBHRSGJI-UHFFFAOYSA-N |
M.W : | 256.36 | Pubchem ID : | 220448 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.54 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 69.62 |
TPSA : | 51.75 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.18 cm/s |
Log Po/w (iLOGP) : | 3.28 |
Log Po/w (XLOGP3) : | 3.78 |
Log Po/w (WLOGP) : | 4.36 |
Log Po/w (MLOGP) : | 3.24 |
Log Po/w (SILICOS-IT) : | 2.97 |
Consensus Log Po/w : | 3.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.61 |
Solubility : | 0.0629 mg/ml ; 0.000245 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.56 |
Solubility : | 0.00705 mg/ml ; 0.0000275 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.87 |
Solubility : | 0.0035 mg/ml ; 0.0000136 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.77 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
27.5% | With sodium hydroxide; In toluene; | Step vi) Production of 2,3-dicyanohydroquinone monohexyl ether 11.3 g (44.1 mM) of n-hexyl p-toluenesulfonate was added to the mixture of 5.0 g (31.3 mM) of dicyanohydroquinone and 37.5 ml of 5% NaOH aqueous solution, followed by 7 hours of stirring under refluxing. After the reaction, the reaction mixture was washed with toluene and the aqueous layer was acidified with HCl. The resultant precipitate was recovered through filtration and dried. To the precipitate, 1 liter of toluene was added. After the insoluble substrate was filtered out, the filtrate was subjected to recrystallization in a refrigerator and further subjected to recrystallization from a mixture solvent of water/methanol to obtain 2.1 g of an objective product (yield: 27.5%). m.p.: 150-153 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In N-methyl-acetamide; | PREPARATION EXAMPLE 2 1.4 g (5 mmol) of the product (8-1) obtained in Preparation Example 1 was dissolved in 20 ml of dimethylformamide, and the solution was added with 0.24 g (6 mmol) of sodium hydride (content: 60%) and stirred at room temperature for one hour. This was followed by addition of 1.5 g (6 mmol) of n-hexyl p-toluenesulfonate and stirring at room temperature for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate, and the obtained organic layer was washed with water and brine dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: toluene/hexane (1/1)) to obtain 1.6 g of (+)-4-benzyloxy-1-(1-hexyloxy-2,2,2-trifluoroethyl)benzene (9-1). Yield: 88%; [α]D20 =+36.6 (c=1, CHCl3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Preparation Example 99 In a flask, 1.4 g (5 mmoles) of the compound (XLIII) obtained in Preparation 98 and 20 ml of dimethylformamide were added to form a solution, and 0.3 g (8 mmoles) of sodium hydride (content: 60%) was added, then stirred at room temperature for 1 hour. Thereafter 2.1 g (8 mmole) of n-hexyl p-toluenesulfonate was added thereto, and stirred at 70-80 C. for 10 hours. After completion of the reaction, the resultant mixture was poured into water, the organic layer thus obtained was washed successively with water and saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate, subjected to silica gel column chromatography (eluent: toluene/ethyl acetate=40/1) to give 1.5 g of (+)-2-benzyloxy-6-(1-hexyloxyethyl)naphthalene (XLII-1) [Yield: 81%, [α]D20 =+53.0 C. (c=1, CHCl3)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | EXAMPLE 1 Into 20 ml of anhydrous dlmethylformamide were dissolved 1.78 g (5 millimole) of the (+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine obtained in Preparation Example [starting material compound (VI)] 70, and then 0.24 g (6 millimole) of 60% sodium hydride was added thereto, followed by stirring at 40 C. for 1 hour. Subsequently, 1.79 g (7 millimole) of hexyl p-toluenesulfonate were added thereto, to subject to reaction at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was poured into 200 ml of water, extracted with 200 ml of toluene, followed by separation thereof, and the organic phase was washed with water sufficiently, followed by drying over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent; toluene: ethyl acetate) to obtain 1.81 g (yield: 82%) of (+)-2-{4-(1-hexyloxyethyl)phenyl}-5-decyloxypyrimidine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; | In DMF solvent, the intermediate compound (Formula VII) and n-hexyl p-toluenesulfonate were reacted in a similar manner to that of process 1.6 in the above-mentioned Example 1 in the presence of a base; potassium carbonate and the product was purified to give a compound shown by formula (VIII, R=n-hexyl), 9-benzyl-2-(3,5-di-tert-butyl-4-methoxymethyloxyphenyl)-6-n-hexyloxypurine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In N-methyl-acetamide; | EXAMPLE 3 A solution consisting of 3.6 g (0.02 mol) of V-1 obtained in Example 1 and 30 ml of dimethylformamide was cooled to 10 C., then added with 0.62 g (0.026 mol) of sodium hydride and kept at 30-35 C. for one hour. The mixture was further added with 7.69 g (0.03 mol) of n-hexyl tosylate at 20-25 C. and reacted at 40-50 C. for 5 hours. The reaction mixture was treated according to Example 1 to obtain 4.60 g (92% yield) of (+)-methyl 4-(1-hexyloxyethyl)benzoate (VII-3). ([alpha]D20 =+60.6 (c=1, CHCl3), nD20 =1.4922). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With 1-methyl-pyrrolidin-2-one; | EXAMPLE 6 A solution of 1.0 g (3.7 mmol) of V-5 obtained in Example 5 and 30 ml of N-methylpyrrolidone was cooled to 5 C., followed by addition of 0.19 g (4.8 mmol) of sodium hydride. The mixture was maintained at 30-35 C. for one hour, then added with 1.23 g (4.8 mmol) of hexyl tosylate at 15-20 C. and reacted at 20-30 C. for 2 hours and further at 40-50 C. for additional 2 hours. The reaction mixture was poured into ice-water and extracted with 60 ml of ethyl acetate. The extract was further treated according to Example 5 to obtain 1.09 g (83% yield) of (+)-ethyl 4'-(1-hexyloxyethyl)-4-biphenylcarboxylate (VII-6). ([α]D20 =+64.5 (c=1.01, CHCl3)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In 1-methyl-pyrrolidin-2-one; | EXAMPLE 11 2.56 g (0.01 mol) of V-9 obtained in Example 9 was dissolved in 20 ml of N-methylpyrrolidone and cooled to 10 C. To this solution was added 0.31 g (0.013 mol) of sodium hydride, followed by standing at 30-35 C. for one hour. The mixture was further added with 3.6 g (0.014 mol) of <strong>[3839-35-8]n-hexyl tosylate</strong> at 20-25 C. and reacted at 40 C. for 5 hours. The reaction mixture was poured into ice-water and extracted with 50 ml of ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure, and the residue was purified by column chromatography to obtain 3.11 g (92% yield) of (+)-benzyl 4-(1hexyloxyethyl)benzoate (VII-11). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.5% | In N-methyl-acetamide; | EXAMPLE 3 A solution of 3.42 g (0.015 mol) of III-1 obtained in Example 1 and 40 ml of dimethylformamide was cooled to 10 C., then added with 0.47 g (0.0196 mol) of sodium hydride and kept at 30-35 C. for one hour. Then 5.76 g (0.0225 mol) of <strong>[3839-35-8]n-hexyl tosylate</strong> was added and the mixture was reacted at 40-45 C. for 5 hours. The reaction mixture was further treated according to Example 1 to obtain 4.42 g (94.5% yield) of (+)-4-benzyloxy-1-(1'-n-hexyloxyethyl)benzene (II-3). ([α]D20 =+58.9 (c=1, CHCl3), nD20 =1.5230). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With potassium carbonate; In 1,4-dioxane; at 40 - 50℃; for 10h; | General procedure: Potassium carbonate (1.00 g, 7.2 mmol) was added to a suspension of compound 1 (1.00 g, 2.7 mmol) and methyl tosylate (0.66 g, 4.0 mmol) in anhydrous dioxane (20 mL), and the mixture was stirred at 40-50 C for 10 h. Chloroform (40 mL) was added to the reaction mixture, which was washed with water (4 × 20 mL). The solvent was evaporated on a rotary evaporator at reduced pressure. The residue obtained in amount of 0.53 g was recrystallized from benzene as colorless crystals of compound 2. Yield: 51% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
122.5 mg | With 1,1,3,3-Tetramethyldisiloxane; [1,3-bis(2,6-di-iso-propylphenyl)imidazol-2-ylidene]copper(I) tert-butoxide; cesium fluoride; In 1,4-dioxane; at 25℃; for 4h;Inert atmosphere; Glovebox; | General procedure: 4.6 General triflation/reduction procedure for primary alcohol deoxygenation A flame-dried reaction flask was pressurized with dry nitrogen then charged with a stir bar, a primary alcohol (2.0mmol, 1.0equiv), and CH2Cl2 (5.0mL). The flask was placed in a dry ice/acetone bath at ca. -78C, and while stirring vigorously, 2,6-lutidine (370μL, 3.2mmol, 1.6equiv) was added, followed by the drop-wise addition of triflic anhydride (460μL, 2.4mmol, 1.2equiv). The reaction mixture was allowed to stir for 15min at -78C before adding HCl (15mL, 1M solution in H2O). The flask was then removed from the dry ice/acetone bath, and after slightly thawing, the reaction mixture was transferred to a separatory funnel and extracted with CH2Cl2 (5×15mL). The organic layers were combined then dried over Na2SO4 before filtration and concentration under vacuum. The resulting crude reaction products were then filtered through a 10g plug of silica gel, which was rinsed with a 1:9 solution of ethyl acetate/hexanes until all of the desired alkyl triflate was recovered based on TLC of the eluent. The product-containing fractions were combined and concentrated under vacuum, and the alkyl triflate products were used immediately without further purification. In a nitrogen-filled glovebox, a dry 20mL vial was charged with a stir bar, followed by cesium fluoride (76mg, 0.50mmol, 1.0equiv), IPrCuOt-Bu 14 (13mg, 0.025mmol, 0.050equiv), and 1,4-dioxane (1.67mL). While stirring at ambient temperature, tetramethyldisiloxane (58μL, 0.33mmol, 0.65equiv) was added, followed by a solution of alkyl triflate (0.50mmol, 1.0equiv) in 1,4-dioxane (1.67mL). The reaction mixture was stirred at ambient temperature for 4h, at which point it was filtered through a 10g plug of silica gel, which was then rinsed with Et2O (20mL). The filtrate was concentrated under vacuum and the crude reaction products were purified by chromatography on silica gel (25g) using a solvent gradient of 0-10% ethyl acetate/hexanes over eight column volumes. 4.6.1.7 p-Toluenesulfonic acid, hexyl ester (72) Compound was isolated as a colorless liquid (122.5 mg, 96% yield). Spectral data match reported literature values. 75 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With 1,1,3,3-Tetramethyldisiloxane; [1,3-bis(2,6-di-iso-propylphenyl)imidazol-2-ylidene]copper(I) tert-butoxide; cesium fluoride; In 1,4-dioxane; at 25℃; for 24h;Inert atmosphere; Glovebox; | General procedure: 4.8 General procedure for the reduction of primary halides In a nitrogen-filled glovebox, a dry 20mL vial was charged with a stir bar, followed by cesium fluoride (76mg, 0.50mmol, 1.0equiv), IPrCuOt-Bu 14 (13mg, 0.025mmol, 0.050equiv), and 1,4-dioxane (1.67mL). While stirring at ambient temperature, tetramethyldisiloxane (58μL, 0.33mmol, 0.65equiv) was added, followed by a solution of alkyl iodide (0.50mmol, 1.0equiv) in 1,4-dioxane (1.67mL). The reaction mixture was stirred at ambient temperature for 24h, at which point it was filtered through a 10g plug of silica gel, which was then rinsed with Et2O (20mL). The filtrate was concentrated under vacuum and the crude reaction products were purified by chromatography on silica gel (25g) using a solvent gradient of 0-10% ethyl acetate/hexanes over eight column volumes. 4.8.1.7 p-Toluenesulfonic acid, hexyl ester (72) Compound was isolated as a colorless liquid (111.6 mg, 87% yield). Spectral data match reported literature values. 75 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium tert-butylate; In tetrahydrofuran; at 0 - 20℃; for 3h; | A solution of triphenymethyl mercaptan (3.94 g, 14.25 mmol) inTHF (25 ml) was added dropwise to a solution of compound 11(2.7 g, 9.5 mmol) and potassium tert-butanolate (3.2 g, 28.5 mmol)in THF (25 ml) at 0 C, then the mixture was warmed to rt andstirred for 3 h before the solutionwas adjusted to pH2 by 1MHCl,the solvent was evaporated in vacuo and redissolved by EA andwashed with water, the organic phases dried with Na2SO4, filtered,concentrated, and purified by silica gel chromatography to afford asyellow solid 13 (3.1 g, 84%). 1H NMR (400 MHz, CDCl3): d 7.42e7.41(m, 6H), 7.40e7.39 (m, 6H), 7.29e7.28 (m, 3H), 2.13 (t, J7.6 Hz, 2H),1.42e1.37 (m, 2H), 1.35e1.14 (m, 6H), 0.79 (t, J6.8 Hz, 3H) ppm. |
84% | With potassium tert-butylate; In tetrahydrofuran; at 20℃; for 3h; | Compound 30 (2.7g, 9 . 5mmol) potassium and tertiary butyl alcohol (3.2g, 28 . 5mmol) dissolved in anhydrous tetrahydrofuran (25 ml), cooled to 0 C, triphenylporphyrin a thiol (3.94g, 14 . 25mmol) dissolved in tetrahydrofuran (25 ml) is dropped into the, go to room temperature stirring 3h, the reaction solution with 1M hydrochloric acid to pH= 2, decompression turns on lathe tetrahydrofuran, diluted with water, extracted with ethyl acetate organic phase (100mLx3), combined with the phase, the organic phase with saturated salt water washing, dry anhydrous sodium sulfate, concentrated, the residue is dissolved in silica gel column chromatography to obtain compound 31 (3.1g, 84%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; for 4h;Reflux; | General procedure: A solution of alkyl 4-methylbenzenesulphonate (40 mmol) in acetonitrile (20 ml) was added to a solution of 2-(N,N-dimethylamino)ethanol (40 mmol) in acetonitrile (20 ml). The reaction mixture was refluxed for 4 h. The solvent was evaporated in vacuum and the crude solid was left for crystallisation from acetone yielding a white, hygroscopic solid as the product. The product was kept in vacuum desiccator over P4O10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In dichloromethane; at 20℃;Inert atmosphere; | General procedure: Procedure A: To a solution of the sulfonic acid (0.164 mmol) in methylene chloride (1.5 mL) was added a 0.4M solution of 1 in methylene chloride dropwise (0.2 mL, 0.082 mmol). The reaction mixture was stirred under argon overnight and then concentrated under reduced pressure at room temperature. The residue was suspended in ether, washed with saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure to yield the sulfonic esters below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | at 105℃; for 72h; | A mixture of 2-methyl-6-nitrobenzothiazole (1 mmol) and hexyl p-toluenesulfonate (1,2 mmol) was heated at temperature of 105 C for 72 h. The solid so formed was dissolved in the minimum hot water amount as possible. After cooling, the aqueous phase was washed with diethyl ether and the solvent was evaporated under reduced pressure almost dryness. The crystals were filtered under reduced pressure. Green crystals. Yield: 16%. mp: 203-203,5 C. IR (υmax/cm-1): 3078, 2948, 2922, 2865, 1607, 1858, 1533, 1508 (NO2), 1456, 1409, 1344 (NO2), 1192 (S=O), 1147, 1119, 1033, 1011, 933, 889, 863, 811, 751, 722, 709, 677. 1H NMR (400 Hz, DMSO-d6): δ (ppm) = 9.41 (d, 1H, J = 2.4 Hz, 7-ArH), 8.63 (dd, 1H, J = 9.3 Hz, 2.3 Hz, 5-ArH), 8.57 (d, 1H, J = 9.3 Hz, 4-ArH), 7.45 (d, 2H, J = 8.0 Hz, 2*ArH Ts), 7.07 (d, 2H, J = 7.8 Hz, 2*ArH Ts), 4.75 (t, 2H, J = 8.0 Hz, NCH2), 3.28 (s, 3H, 2-CH3), 2.26 (s, 3H, CH3 Ts), 1.83 (qt, J = 7.8 Hz, 2H, NCH2CH2), 1.51-1.36 (m, 2H, N(CH2)2CH2), 1.32-1.26 (m, 4H, N(CH2)3CH2CH2), 0.87 (t, 3H, J = 6.7 Hz, N(CH2)5CH3). 13C NMR (101 MHz, DMSO-d6): δ (ppm) = 182.9 (C), 146.1 (C), 145.7 (C), 144.3 (C), 137.6 (C), 130.2 (C), 128.0 (2*ArCH Ts), 125.5 (2*ArCH Ts), 124.2 (5-ArCH), 121.8 (7-ArCH), 118.1 (4-ArCH), 49.8 (NCH2), 30.8 (CH2), 27.7 (NCH2CH2), 25.5 (N(CH2)2CH2), 21.9 (CH2), 20.8 (CH3 Ts), 17.5 (2-CH3), 13.9 (N(CH2)5CH3). HRMS (ESI-TOF) m/z: 279.1170 (279.1162 calcd for C14H19N2O2S, [M+]). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | at 120℃; for 25h; | A mixture of 6-acetamide-2-methylbenzothiazole (1 mmol) and hexyl p-toluenesulfonate (1,2 mmol) was heated at temperature of 120 C for 25 h. The solid so formed was recrystallized from dichloromethane. After cooling, diethyl ether was added and the precipitate was filtered under reduced pressure. Orange powder. Yield: 63%. mp: 187-189 C. IR (υmax/cm-1): 3247, 3188, 3116, 3033, 2957, 2923, 2856, 1685 (C=O), 1592, 1560, 1438, 1373, 1345, 1274, 1218, 1181 (S=O), 1122, 1052, 1032, 1009, 901, 826, 814, 680. 1H NMR (400 Hz, DMSO-d6): δ (ppm) = 10.58 (s, 1H, NH), 8.72 (d, 1H, J = 2.0 Hz, 7-ArH), 8.15 (d, 1H, J = 8.2 Hz, 4-ArH), 7.79 (dd, 1H, J = 9.2 Hz, 2.1 Hz, 5-ArH), 7.48 (d, 2H, J = 8.0 Hz, 2*ArH Ts), 7.10 (d, 2H, J = 7.9 Hz, 2*ArH Ts), 4.58 (t, 2H, J = 7.9 Hz, NCH2), 3.09 (s, 3H, 2-CH3), 2.24 (s, 3H, CH3 Ts), 2.10 (s, 3H, NHCOCH3), 1.78 (qt, 2H, J = 7.7 Hz, NCH2CH2), 1.36 (qt, 2H, J = 7.3 Hz, N(CH2)2CH2), 1.30-1.17 (m, 4H, N(CH2)3CH2CH2), 0.81 (t, 3H, J = 7.0 Hz, N(CH2)5CH3). 13C NMR (101 MHz, DMSO-d6): δ (ppm) = 174.9 (C), 169.1 (C), 145.5 (C), 139.1 (C), 137.7 (C), 136.3 (C), 130.1 (C), 128.1 (2*ArCH Ts), 125.5 (2*ArCH Ts), 121.8 (5-ArCH), 117.1 (4-ArCH), 112.8 (7-ArCH), 49.2 (NCH2), 30.8 (CH2), 27.8 (NCH2CH2), 25.8 (N(CH2)2CH2), 24.1 (NHCOCH3), 21.9 (CH2), 20.8 (CH3 Ts), 16.6 (2-CH3), 13.9 (N(CH2)5CH3. HRMS (ESI-TOF) m/z: 291.1522 (291.1526 calcd for C16H23N2OS, [M+]). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.3% | 1.7 g (4.5 mmol) of 10 and 2.1 g (6.8 mmol) of cesium carbonate were added to 9 mL of N,N-dimethylformamide under an oil bath of 55 C for 13 min.1.51 g (5.9 mmol) of n-hexyl p-toluenesulfonate was added in an oil bath at 60 C.The reaction was stirred for 15 h, then brine was added and ethyl acetate was evaporated.The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated.The residue was subjected to silica gel column chromatography (dichloromethane:methanol = 20:1) to give 2.23 g of colorless viscous solid 13d, yield 81.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.6% | With tetrabutylammomium bromide; sodium hydroxide; In water; toluene; at 80℃; for 2h;Inert atmosphere; | General procedure: Under a nitrogen stream,In a three-necked 200 mL flask equipped with a thermometer,10 g (61 mmol) of 2-hydrazinobenzothiazole,50 ml of toluene,10 ml of water,3.6 g (1.5 eq) of sodium hydroxide, 2.0 g (0.1 eq) of tetrabutylammonium bromide,Add 12 g (1.2 eq) of bromohexane,While stirringThe reaction was performed at 80 C. for 2 hours.After the reaction,Cool to room temperature,After removing the aqueous phase,Washed with water and 1N hydrochloric acid.By adding 100 ml of heptane to the obtained organic phase,A precipitate was deposited. Filter the precipitate,By drying the obtained crystals,Thus, 11.4 g (46 mmol, yield: 75.5%) of the target compound, Compound 1, was obtained. |
40% | With potassium hydroxide; In N,N-dimethyl-formamide; at 80℃; for 4h; | 5.0 g (30 mmol) of 2-hydrazinobenzothiazole,Potassium hydroxide 2.5 g (45 mmol)Is added to N, N-dimethylformamide (90 mL),Heated at 80 degrees.After reaching a predetermined temperature,9.2 g (36 mmol) of hexyl p-toluenesulfonate was added dropwise.After the dripping endStir for 4 hours.After the reaction,Add 10 ml of water and extract,The solvent was distilled off.The residue is purified by silica gel chromatography.By evaporating the solvent, the formula (1-1-5)Were obtained 3.0 g (12 mmol, 40% yield) of Intermediate 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With tetrabutylammomium bromide; sodium hydroxide; at 100℃; for 8h; | Taking paratoluene sulfonic acid hexyl 2.56 g (0.01 µM), at room temperature by adding 0.62 g (0.0036 µM) to bromine, adding 0.05 g ammonium bromide [...] transfer catalyst, heating up to 100 C dropwise 25% sodium hydroxide solution of 1.6 g (0.01 µM), maintaining the temperature reaction 8 h after, to room temperature, extracted with ethyl acetate, dried and filtered, rotary evaporation, to obtain the dark purple viscous liquid, by silica gel column to obtain a pale yellow liquid 0.99 g, N, N - dihexylacrylamide to aniline yield is 81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With tetrabutylammomium bromide; sodium hydroxide; at 100℃; for 8h; | Taking paratoluene sulfonic acid hexyl 2.56 g (0.01 µM), at room temperature by adding 0.46 g (0.0036 µM) to P-chloroaniline, adding 0.05 g ammonium bromide [...] transfer catalyst, heating up to 100 C dropwise 25% sodium hydroxide solution of 1.6 g (0.01 µM), maintaining the temperature reaction 8 h after, to room temperature, extracted with ethyl acetate, dried and filtered, rotary evaporation, can be dark purple viscous liquid, by silica gel column to obtain a pale yellow liquid 0.95 g, N, N - dihexylacrylamide to P-chloroaniline of yield is 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With tetrabutylammomium bromide; sodium hydroxide; at 100℃; for 8h; | Taking paratoluene sulfonic acid hexyl 2.56 g (0.01 µM), at room temperature by adding 0.38 g (0.0036 µM) P-toluidine, adding 0.05 g ammonium bromide [...] transfer catalyst, heating up to 100 C dropwise 25% sodium hydroxide solution of 1.6 g (0.01 µM), maintaining the temperature reaction 8 h after, to room temperature, extracted with ethyl acetate, dried and filtered, rotary evaporation, can be dark purple viscous liquid, by silica gel column to obtain a pale yellow liquid 0.80 g, N, N - dihexylacrylamide toluidine of yield is 81%. |
Tags: 3839-35-8 synthesis path| 3839-35-8 SDS| 3839-35-8 COA| 3839-35-8 purity| 3839-35-8 application| 3839-35-8 NMR| 3839-35-8 COA| 3839-35-8 structure
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Heptadecan-9-yl 4-methylbenzenesulfonate
Similarity: 0.96
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
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. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
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 |
Sorry,this product has been discontinued.
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