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HazMat fee for 500 gram (Estimated)
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Structure of 51419-59-1 * 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 tert-butylhypochlorite In water; acetonitrile at 0 - 20℃;
General procedure: Alkyl halide (or sulfate) (5 mmol) and thiourea (0.381 g, 5 mmol) were heated at reflux in EtOH (5 mL) for 1 h. After removal of the solvent in vacuum and washing with Et2O (3 × 5 mL), the corresponding S-alkyl isothiourea salt was obtained as a white solid in almost quantitative yield. Without purification, the product was transferred into a three-necked round-bottom flask equipped with a thermometer and an addition funnel in an ice-bath, followed by addition of water (0.45mL) and MeCN (10 mL). To the resultant vigorously stirred mixture was added dropwise a solution of t-BuOCl (2.86 mL) in MeCN (5 mL), keeping the inner temperature at 0–20 °C. The mixture was then stirred for 30 min. Removal of the solvent under vacuum, addition of Et2O (15 mL), washing with H2O (2 × 10 mL), drying over Na2SO4, and concentration under vacuum gave the desired product in high purity. The product was further purified by recrystalization from petroleum ether–EtOAc.
0.665 g
With hydrogenchloride; sodium chlorite In acetonitrile at 10 - 20℃; for 0.5 h; Green chemistry
General procedure: Step 1. An alkyl halide or mesylate (5 mmol) and thiourea (0.381 g, 5 mmol) wererefluxed in 5 mL of ethanol for 1 h. After removal of the solvent in vacuum thecorresponding S-alkyl isothiourea salt was obtained as white solid or sticky oil.Step 2. A 50 mL three-necked flask equipped with a thermometer and asolid-addition funnel was immersed in an ice-bath. To the flask was sequentiallyadded NaClO2 solid (for isothiouronium chlorides or sulfonate, 1.61 g, 15 mmol; forisothiouronium bromides, 2.14 g, 20 mmol, 85percent purity), MeCN (10 mL), and thenconc. HCl (for isothiouronium chlorides or sulfonate, 3 mL; for isothiouroniumbromides, 4 mL) during 1 min at such a rate that the inner temperature was maintainedless than 10 °C. Then S-alkyl isothiourea salt was slowly added througth the solidaddition-funnel to keep the inner temperature less than 20 °C. After the addtion, theresulting mixture was stirred for another 30 min. Then 25 mL of water was added, and the resultant mixture was evaporated in vacuum at 15 °C to remove acetonitrile. Afteraddition of 100 mL of water, the solid products were obtained by filtration on aBuchner funnel and dried under an infrared lamp, while the liquid products wereobtained by extraction with 15 mL of ethyl acetate, drying with Na2SO4, andconcentration in vacuum.For 1,4-dibromobutane, the amounts of thiourea, NaClO2 solid, MeCN, and conc.HCl were doubled.
0.899 g
With sodium hypochlorite; sulfuric acid In diethyl ether; water at 0 - 20℃; for 0.5 h; Green chemistry
General procedure: The appropriate alkyl halide (or mesylate) (5 mmol) and thiourea (0.381 g, 5 mmol) were refluxed in EtOH (5 mL) for 1 h. After removal of the solvent in vacuum and washing with Et2O (3 × 5 mL), the corresponding S-alkyl isothiourea salt was obtained as a white solid or sticky oil in an almost quantitative yield. Without purification, the product was transferred into a three-necked round-bottomed flask equipped with a thermometer and an addition funnel in an ice-bath. Then, 6 M H2SO4 (2 mL), followed by Et2O (30 mL) were added. To the resultant vigorously stirred mixture was added dropwise 5percent bleach (for alkyl chlorides and mesylates, 30 mL; foralkyl bromides, 37.5 mL) by keeping the inner temperature 0–20 °C (for the preparation of alkanedisulfonyl dichlorides, 0.762 g, 10 mmol thiourea, 4 mL of 6 M H2SO4, 50 mL of Et2O, and 75 mL of 5percent bleach were used). After the addition, the mixture was stirred for another 30 min. The mixture was partitioned in a separatory funnel, and the ethereal phase was washed with brine (25 mL), dried (Na2SO4), and evaporated in vacuum to afford the desired product. The oily products were extracted with CHCl3 (3 × 2.5 mL) and evaporated to remove the by-product, bromine. If necessary, the products can be dissolved in minimal PE–EtOAc (5:1) and filtered through a column of silica gel (h = 5 cm) with PE–EtOAc (5:1) as eluent to remove the impurities (Table 2).
Reference：
[1] Synthesis (Germany), 2015, vol. 47, # 20, p. 3186 - 3190
[2] European Journal of Organic Chemistry, 2012, # 26, p. 5028 - 5037,10
[3] European Journal of Organic Chemistry, 2012, # 26, p. 5028 - 5037
[4] Journal of the American Chemical Society, 1987, vol. 109, # 24, p. 7472 - 7477
[5] Synthesis (Germany), 2013, vol. 45, # 12, p. 1675 - 1682
[6] Synlett, 2013, vol. 24, # 16, p. 2165 - 2169
[7] Organic Syntheses, 2014, vol. 91, p. 116 - 124
[8] Synthesis (Germany), 2014, vol. 46, # 2, p. 225 - 229
2
[ 104-81-4 ]
[ 51419-59-1 ]
Reference：
[1] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9350 - 9359
[2] Organic Letters, 2004, vol. 6, # 23, p. 4285 - 4288
[3] ACS Catalysis, 2017, vol. 7, # 8, p. 5357 - 5362
3
[ 104-82-5 ]
[ 51419-59-1 ]
Reference：
[1] Tetrahedron Letters, 1984, vol. 25, # 40, p. 4553 - 4556
[2] Synthesis (Germany), 2013, vol. 45, # 12, p. 1675 - 1682
[3] Organic Syntheses, 2014, vol. 91, p. 116 - 124
[4] Synthesis (Germany), 2014, vol. 46, # 2, p. 225 - 229
[5] Synthesis (Germany), 2015, vol. 47, # 20, p. 3186 - 3190
[6] Angewandte Chemie - International Edition, 2015, vol. 54, # 29, p. 8515 - 8519
[7] Angewandte Chemie - International Edition, 2017, vol. 56, # 19, p. 5272 - 5276[8] Angew. Chem., 2017, vol. 129, # 19, p. 5356 - 5360,5
[9] European Journal of Organic Chemistry, 2018, vol. 2018, # 15, p. 1774 - 1784
4
[ 104-82-5 ]
[ 51419-59-1 ]
Yield
Reaction Conditions
Operation in experiment
46%
With sodium hydroxide; thionyl chloride; sodium sulfite In <i>N</i>-methyl-acetamide; ice-water; Petroleum ether
EXAMPLE 1 Synthesis of p-methylbenzylsulfonyl chloride In a 10percent aqueous solution of sodium hydroxide (250 ml) is dissolved sodium sulfite (67 g, 0.53 mol), followed by the addition of p-methylbenzyl chloride (75 g, 0.53 mol). The mixture is refluxed with stirring for 4 hours. The reaction mixture is diluted two-fold with water and filtered when hot. The filtrate is cooled. The crystals of sodium p-methylbenzylsulfonate are collected by filtration. Yield 51 g (46percent). In dimethylformamide (90 ml) is dispersed sodium p-methylbenzylsulfonate (30 g, 0.145 mol) which is sufficientry dry. The dispersion is cooled to -10° C. and under stirring, thionyl chloride (19.2 ml, 0.29 mol) is added dropwise. The mixture is stirred at room temperature for 3 hours and poured in ice-water (500 g) and extracted with ether (3 times, 150 ml each). The ethereal layers are combined, washed twice with cold water and dried over sodium sulfate. The ether is distilled off and petroleum ether is added to the crystalline residue, followed by cooling. The crystals are collected by filtration. Yield 23.5 g (78percent), m.p. 80°-81° C.
Reference：
[1] Patent: US4159979, 1979, A,
5
[ 4498-99-1 ]
[ 51419-59-1 ]
Reference：
[1] Synlett, 2011, # 16, p. 2315 - 2320
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 2, p. 383 - 386
General procedure: Various substituted BnCl 9a?k (2.5 mmol) and thiourea (0.19 g,2.5 mmol) were refluxed together in EtOH (2.5 mL) for 1 h. After removalof EtOH at reduced pressure, the obtained solid was slowly added to a mixture of NCS (1.33 g, 10 mmol), 2M HCl (0.68 mL) and MeCN (4 mL) over 30 min. After completion of the reaction, the MeCN was removed on a rotary evaporator. Then H2O (3 mL) was added, and the white solid was filtered and dried under an infrared lamp to afford 10a?k (70percent?93percent), respectively, which did not require further purification.Then, 10a?k were treated with ammonia solution (1 mL) inacetone (2 mL) at 0 °C for 4 h. After removal of acetone at reducedpressure, the crude was extract with EtOAc, and the combined organiclayers were washed with H2O, and brine. After drying over Na2SO4,filtering, and concentrating of the organic phase, the resulting yellowsolid 11a?k was used directly in the next step. Finally, 11a?k and ethylchloroformate (1.2 eq) were refluxed together in the presence K2CO3(1.5 eq) in acetone (5.0 mL) for 4 h obtained 12a?k.
With tert-butylhypochlorite; In water; acetonitrile; at 0 - 20℃;
General procedure: Alkyl halide (or sulfate) (5 mmol) and thiourea (0.381 g, 5 mmol) were heated at reflux in EtOH (5 mL) for 1 h. After removal of the solvent in vacuum and washing with Et2O (3 × 5 mL), the corresponding S-alkyl isothiourea salt was obtained as a white solid in almost quantitative yield. Without purification, the product was transferred into a three-necked round-bottom flask equipped with a thermometer and an addition funnel in an ice-bath, followed by addition of water (0.45mL) and MeCN (10 mL). To the resultant vigorously stirred mixture was added dropwise a solution of t-BuOCl (2.86 mL) in MeCN (5 mL), keeping the inner temperature at 0?20 °C. The mixture was then stirred for 30 min. Removal of the solvent under vacuum, addition of Et2O (15 mL), washing with H2O (2 × 10 mL), drying over Na2SO4, and concentration under vacuum gave the desired product in high purity. The product was further purified by recrystalization from petroleum ether?EtOAc.
0.665 g
With hydrogenchloride; sodium chlorite; In acetonitrile; at 10 - 20℃; for 0.5h;Green chemistry;
General procedure: Step 1. An alkyl halide or mesylate (5 mmol) and thiourea (0.381 g, 5 mmol) wererefluxed in 5 mL of ethanol for 1 h. After removal of the solvent in vacuum thecorresponding S-alkyl isothiourea salt was obtained as white solid or sticky oil.Step 2. A 50 mL three-necked flask equipped with a thermometer and asolid-addition funnel was immersed in an ice-bath. To the flask was sequentiallyadded NaClO2 solid (for isothiouronium chlorides or sulfonate, 1.61 g, 15 mmol; forisothiouronium bromides, 2.14 g, 20 mmol, 85percent purity), MeCN (10 mL), and thenconc. HCl (for isothiouronium chlorides or sulfonate, 3 mL; for isothiouroniumbromides, 4 mL) during 1 min at such a rate that the inner temperature was maintainedless than 10 °C. Then S-alkyl isothiourea salt was slowly added througth the solidaddition-funnel to keep the inner temperature less than 20 °C. After the addtion, theresulting mixture was stirred for another 30 min. Then 25 mL of water was added, and the resultant mixture was evaporated in vacuum at 15 °C to remove acetonitrile. Afteraddition of 100 mL of water, the solid products were obtained by filtration on aBuchner funnel and dried under an infrared lamp, while the liquid products wereobtained by extraction with 15 mL of ethyl acetate, drying with Na2SO4, andconcentration in vacuum.For 1,4-dibromobutane, the amounts of thiourea, NaClO2 solid, MeCN, and conc.HCl were doubled.
0.899 g
With sodium hypochlorite; sulfuric acid; In diethyl ether; water; at 0 - 20℃; for 0.5h;Green chemistry;
General procedure: The appropriate alkyl halide (or mesylate) (5 mmol) and thiourea (0.381 g, 5 mmol) were refluxed in EtOH (5 mL) for 1 h. After removal of the solvent in vacuum and washing with Et2O (3 × 5 mL), the corresponding S-alkyl isothiourea salt was obtained as a white solid or sticky oil in an almost quantitative yield. Without purification, the product was transferred into a three-necked round-bottomed flask equipped with a thermometer and an addition funnel in an ice-bath. Then, 6 M H2SO4 (2 mL), followed by Et2O (30 mL) were added. To the resultant vigorously stirred mixture was added dropwise 5percent bleach (for alkyl chlorides and mesylates, 30 mL; foralkyl bromides, 37.5 mL) by keeping the inner temperature 0?20 °C (for the preparation of alkanedisulfonyl dichlorides, 0.762 g, 10 mmol thiourea, 4 mL of 6 M H2SO4, 50 mL of Et2O, and 75 mL of 5percent bleach were used). After the addition, the mixture was stirred for another 30 min. The mixture was partitioned in a separatory funnel, and the ethereal phase was washed with brine (25 mL), dried (Na2SO4), and evaporated in vacuum to afford the desired product. The oily products were extracted with CHCl3 (3 × 2.5 mL) and evaporated to remove the by-product, bromine. If necessary, the products can be dissolved in minimal PE?EtOAc (5:1) and filtered through a column of silica gel (h = 5 cm) with PE?EtOAc (5:1) as eluent to remove the impurities (Table 2).
(3aR,5R,5aR,8R,8aR,8bR)-2,2-Dimethyl-5-phenylselanylmethyl-8-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-7-p-tolylmethanesulfonyl-octahydro-[1,3]dioxolo[4,5-e]isoindol-6-one[ No CAS ]
8.4 Preparation of p-methylhalobenzylsulfonyl Chloride 1.0 g of p-methylbenzyl bromide and 1 equivalent of thiourea were added to 40 ml of ethanol and then slowly heated to reflux and the solution turned clear. After 4-6 hours of reaction, the reaction solution was concentrated to give a white solid. 10 ml of acetonitrile and 4 ml of concentrated hydrochloric acid were added. The temperature was controlled below 5-10 C., 2.25 g of sodium chlorite was added in batches with intense stirring. The reaction was performed at 15-20 C. for 8-16 hours. The reaction was stopped by adding water and extracted with ethyl acetate for three times. The extract liquor was concentrated to give p-methylbenzylsulfonyl chloride. The crude product was used directly in the next step without purification.
2-(6-methyl-2-oxo-3-<i>p</i>-tolylmethanesulfonylamino-2<i>H</i>-pyridin-1-yl)-<i>N</i>-(4,5,6,7-tetrahydro-2<i>H</i>-indazol-5-ylmethyl)-acetamide[ No CAS ]
<i>N</i>-(2-amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-2-(6-methyl-2-oxo-3-<i>p</i>-tolylmethanesulfonylamino-2<i>H</i>-pyridin-1-yl)-acetamide[ No CAS ]
(1R,1'R,3R,4R,5R)-1-[(tert-butyldimethylsilyl)-oxy]-3,4-(isopropylidenedioxy)-5-[1'-(4-methylphenyl)methanesulfonamide-2'-oxopropyl]cyclohexane[ No CAS ]
(1R,1'R,2'S,3R,4R,5R)-1-[(tert-butyldimethylsilyl)-oxy]-5-[2'-hydroxy-1'-[(4-methylphenyl)methanesulfonamide]propyl]-3,4-(isopropylidenedioxy)cyclohexane[ No CAS ]
(1R,1'R,2'R,3R,4R,5R)-1-[(tert-butyldimethylsilyl)-oxy]-5-[2'-hydroxy-1'-[(4-methylphenyl)methanesulfonamide]propyl]-3,4-(isopropylidenedioxy)cyclohexane[ No CAS ]
(1R,1'R,2'S,3R,4R,5R)-5-[2'-acetoxy-1'-[(4-methylphenyl)methanesulfonamide]propyl]-1-(tert-butyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexane[ No CAS ]
sodium salt of 4-(4-t-butyloxycarbonyl)-piperazinyl-indole[ No CAS ]
[ 51419-59-1 ]
4-Piperazinyl-1-(4-methylphenylmethanesulfonyl)-1H-indole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
9 mg (13%)
EXAMPLE 58 4-Piperazinyl-1-(4-methylphenylmethanesulfonyl)-1H-indole (Scheme 1) The title compound was prepared according to Method 5 from <strong>[51419-59-1]4-methylphenylmethanesulfonyl chloride</strong> and sodium salt of 4-(4-t-butyloxycarbonyl)-piperazinyl-indole (stock solution A) to give 9 mg (13percent) of a white solid: 1H-NMR (CD3OD) delta 7.46 (d, 1H, J=8.4 Hz) 7.24-7.18 (m, 1H), 7.06 (d, 1H, J=4.0 Hz) 6.95-6.85 (m, 3H), 6.76-6.64 (m, 3H) 4.65 (s, 2H) 3.47-3.35 (m, 8H) 2.24 (s, 3H); MS (ESI) 370.1 (M+H)+; Purity (HPLC) 95percent.
4-methylphenylmethanesulfonic acid,sodium salt[ No CAS ]
[ 51419-59-1 ]
Yield
Reaction Conditions
Operation in experiment
51 g (46%)
With sodium hydroxide; thionyl chloride; sodium sulfite; In N-methyl-acetamide; ice-water; Petroleum ether;
EXAMPLE 1 Synthesis of p-methylbenzylsulfonyl chloride In a 10percent aqueous solution of sodium hydroxide (250 ml) is dissolved sodium sulfite (67 g, 0.53 mol), followed by the addition of p-methylbenzyl chloride (75 g, 0.53 mol). The mixture is refluxed with stirring for 4 hours. The reaction mixture is diluted two-fold with water and filtered when hot. The filtrate is cooled. The crystals of sodium p-methylbenzylsulfonate are collected by filtration. Yield 51 g (46percent). In dimethylformamide (90 ml) is dispersed sodium p-methylbenzylsulfonate (30 g, 0.145 mol) which is sufficientry dry. The dispersion is cooled to -10° C. and under stirring, thionyl chloride (19.2 ml, 0.29 mol) is added dropwise. The mixture is stirred at room temperature for 3 hours and poured in ice-water (500 g) and extracted with ether (3 times, 150 ml each). The ethereal layers are combined, washed twice with cold water and dried over sodium sulfate. The ether is distilled off and petroleum ether is added to the crystalline residue, followed by cooling. The crystals are collected by filtration. Yield 23.5 g (78percent), m.p. 80°-81° C.
With sodium hydrogencarbonate; In dichloromethane; water; for 96h;
The product of step (v) (360 mg) was dissolved in DCM (5 ml), this was followed by addition of a solution of NaHCO3 (218 mg) in water (5 ml). (4-methylphenyl)methane sulfonyl chloride (280 mg) was added portionwise and stirred for 1 day, then additional NaHCO3 and sulfonyl chloride were added and stirred for 3 days overall. The reaction was diluted with water and extracted with DCM (.x.3). The combined organic layers were washed (brine), dried (MgSO4) then concentrated under reduced pressure to give the sub-title compound as a pale yellow oil, yield 210 mg.MS: ESI(+ve) 479 (M+H)
General procedure: A two-step one-pot method for preparing an abscisic acid receptor agonist:Add p-methylbenzyl mercaptan to acetonitrileAnd then adding a chlorinating reagent,Point plate monitoring, after the reaction, move into the ice water bath,Add 4 equivalents of an acid binding agent such as pyridine.After the addition, 7-amino-N-propylquinolinone in acetonitrile was slowly added dropwise.The plate is monitored for reaction, after the reaction, pickling, drying,Further, the abscisic acid receptor agonist can be obtained by column chromatography or recrystallization,
General procedure: Sodium hydride (60percent dispersion in mineral oil) (18 mg, 0.45 mmol) was added to a solution of 2-(4-(Piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one (4) (50 mg, 0.15 mmol) in DMF (10 mL), and the mixture was heated at 100 °C. Appropriate sulfonyl chloride (0.22 mmol) in DMF (3 mL) was added slowly to the reaction mixture. The mixture was stirred at 100 °C for 16 h. After cooling, saturated NaHCO3 solution was added. The reaction mixture was extracted with ethyl acetate and the organic phase was washed with brine. The organic phase was dried over MgSO4 and evaporated in vacuo. The residue was washed with ethyl acetate/hexane (1:10) and purified by column chromatography (ethyl acetate) to provide 2-(4-(4-(substituted)-sulfonyl)piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one.
With pyridine; In dichloromethane; at 0 - 20℃; for 16.5h;
General procedure: To a stirred solution of 17-amino-1,3,5(10)-estratrien-3-ol (0.38 mmol) in dry pyridine (3 mL) at 0 °C was added a solution of the sulfonyl chlorides (0.40 mmol) in dichloromethane (1 mL) via a syringe pump over 30 min. After addition, the reaction was stirred for 16 h at room temperature. The pyridine was removed under vacuum, the residue was dissolved in ethyl acetate, washed with water and brine then dried (Na2SO4,), filtered, and concentrated and the residue purified by column chromatography.
Potassium tert-butoxide (93.8 mg, 836 mumol) was added to a solution of 2-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide (110 mg, 380 mumol) in THF (10 ml) in DMF (2 ml) [Comment: please check]. After 10 min., the reaction mixture was cooled by an ice bath and then a solution of <strong>[51419-59-1](4-methylphenyl)methanesulfonyl chloride</strong> (93.7 mg, 458 mumol) in THF (2 ml) was added. After 70 min., EtOAc and 1 N NaOH aqueous solution were added. The organic phase was extracted with EtOAc and then with DCM. The combined organic phases were washed with water, and brine, dried over Na2SO4 and evaporated to dryness. Chromatography (silica gel, 0 to 2percent MeOH in DCM) provided the title compound as a pale yellow solid (0.080 g; 46percent). LCMS: m/z=457 (MH+).
6-amino-8-methyl-1-prop-2-ynyl-3,4-dihydroquinolin-2-one[ No CAS ]
N-(8-methyl-2-oxo-1-prop-2-ynyl-3,4-dihydroquinolin-6-yl)-1-(p-tolylmethanesulfonamide)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 0 - 20℃; for 4h;
To a solution of 6-amino-8-methyl-1-prop-2-ynyl-3,4-dihydroquinolin-2-one (0.1 mmol) in ethyl acetate (0.5 ml) was added Huenig?s base (0.15 mmol). The reaction mixture was cooled to 0 °C in an ice-ethanol bath. A solution of <strong>[51419-59-1]p-tolylmethanesulfonyl chloride</strong> (0.15 mmol) in ethyl acetate (0.75 ml) was added dropwise and the reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was concentrated. The remaining mixture was diluted with N,N-dimethylacetamide (0.3 ml) and methanol (1.25 ml) and purified by HPLC to give N-(8-methyl-2-oxo-1-prop-2-ynyl-3,4-dihydroquinolin-6-yl)-1- (p-to lyl)methanesulfonamide, compound 1.079. Compounds were identified by UPLC-MS: Retention time (RT) = 1.33mm; M (calculated): 382.14; (M+H) (measured): 383.06
1-allyl-6-amino-3-methyl-3,4-dihydroquinolin-2-one[ No CAS ]
C21H24N2O3S[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 7h;
1-allyl-6-amino-3-methyl-3,4-dihydroquinolin-2-one (130mg) was dissolved in CH2Cl2 (3m1) and cooled to 0°C. iPr2NEt (117mg) and p-tolylmethanesulfonylchloride (129mg) were added. While warming to room temperature, the reaction was stirred for 7h, diluted with CH2C12 and washed with NaHCO3 (aq) and HC1(aq). The organic layer was concentrated and purified by chromatography to give 140mg of product.1HNMR (CDC13, 400MHz) = 7.17 (m, 4H), 6.90 (m, 2H), 6.30 (s, 1H), 5.85 (m, 1H), 5.10 (m, 2H), 4.50 (m, 2H), 4.28 (s, 2H), 2.9-2.6 (m, 3H), 2.33 (s, 3H), 1.22 (d, 3H).
N-(2-oxo-1-propyl-6-quinolyl)-1-(p-tolyl)methanesulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
228 mg
With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 20℃; for 22h;
3) Compound 1.001 [0173] 6-amino- l-propyl-quinolin-2-one (245 mg) was dissolved in ethyl acetate (5 mL), and diisopropylethylamine (0.518 mL) and p-tolylmethansulfonylchloride (0.248 g) were added. The reaction was stirred for 22 h at room temperature, diluted with CH2C12 and washed with water, 5% HC1 (aq) and brine. The combined aqueous phases were extracted again with ethyl acetate and the combined organic phases were concentrated and crystallized from MeOH/diethyl ether. Further purification by chromatography provided 228 mg of Compound 1.001. 1H NMR (CDC13, 400MHz) delta = 7.58 (d, 1H), 7.35-7.15 (m, 7H), 6.82 (d, 1H), 6.40 (bs, 1H), 4.30 (s, 2H), 4.23 (m, 2H),2.34 (s, 3H), 1.75 (m, 2H), 1.03 (t, 3H).
1.3 g
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;
1.0 g of 6-amino-1-propyl-2(1H)-quinolinone and 1.2 equivalents of <strong>[51419-59-1]p-methylbenzylsulfonyl chloride</strong> were added to 20 ml of DMF, and 3 equivalents of potassium carbonate was added as an acid binding agent. The reaction was maintained at room temperature and stirred for 12-16 hours. After that, ice water was added and the mixture was extracted with ethyl acetate for three times and the organic phase was combined and dried over anhydrous sodium sulfate. The organic phase was concentrated and the crude product was subjected to silica gel column chromatography to give 1.3 g of compound 1022B with a yield of 70percent. (0326) 1HNMR (400 MHz, DMSO-d6): delta 0.95 (t, 3H), 1.62 (m, 2H), 2.27 (s, 3H), 4.18 (t, 2H), 4.42 (s, 2H), 6.60 (d, 1H), 7.12-7.17 (m, 4H), 7.40 (d, 1H), 7.45 (s, 1H), 7.55 (d, 1H), 7.83 (d, 1H) ppm; 13CNMR (100 MHz, DMSO-d6) delta 11.53, 20.99, 21.54, 43.35, 57.34, 116.08, 119.20, 121.17, 122.14, 124.01, 126.89, 129.46, 131.34, 133.02, 135.97, 138.12, 139.45, 161.12 ppm.
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