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[ CAS No. 88040-88-4 ] {[proInfo.proName]}

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Product Details of [ 88040-88-4 ]

CAS No. :88040-88-4 MDL No. :MFCD03424997
Formula : C9H11ClO3S Boiling Point : -
Linear Structure Formula :- InChI Key :VHCODCZMAYFSHT-UHFFFAOYSA-N
M.W : 234.70 Pubchem ID :2758862
Synonyms :

Safety of [ 88040-88-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P312-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P330-P363-P405-P501 UN#:1759
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 88040-88-4 ]

* 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.

  • Downstream synthetic route of [ 88040-88-4 ]

[ 88040-88-4 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 88040-88-4 ]
  • (R,R)-1,2-diaminocyclohexane tartrate [ No CAS ]
  • C24H34N2O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In dichloromethane for 1h; Ambient temperature;
  • 2
  • [ 1515-95-3 ]
  • [ 88040-88-4 ]
YieldReaction ConditionsOperation in experiment
53% With chlorosulfonic acid; at 0 - 20℃; for 2h; lii) 5-Ethyl-2-methoxybenzenesulfonyl chloride I112 1-Ethyl-4-methoxybenzene (5.0 g, 37 mmol) was added dropwise to chlorosulfonic acid (20 ml.) at 0 C and the mixture was stirred at RT for 2 h then poured onto ice and extracted with EtOAc (50 ml. x 3). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Pet. ether/EtOAc = 100/1 to 30/1) [116] to give the title compound (4.6 g, 53%) as a white solid. LCMS-D: Rt2.70 min; m/z 256.9 [M+Na]+.
53% With chlorosulfonic acid; at 0 - 20℃; for 2h; 1-Ethyl-4-methoxybenzene (5.0 g, 37 mmol) was added dropwise to chlorosulfonic acid (20 ml.) at 0 C and the mixture was stirred at room temperature for 2 h then poured onto ice and extracted with EtOAc (50 ml. x 3). The combined organic extracts were dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether/EtOAc = 100/1 to 30/1) to give the title compound I19 (4.6 g, 53%) as a white solid. LCMS-B (ES-API): Rt2.70 min; m/z 256.9 [M+Na]+.
YieldReaction ConditionsOperation in experiment
Rk. mit. Zinkpulver, Red., -> 3-Ethyl-6-methoxy-thiophenol;
YieldReaction ConditionsOperation in experiment
4-Ethyl-anisol, Chlorsulfurierung nach Stewart;
  • 5
  • [ 123-07-9 ]
  • [ 88040-88-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / acetone 2: ClSO3H / 3 h / Ambient temperature
  • 6
  • [ 88040-88-4 ]
  • [ 19790-96-6 ]
  • 5-ethyl-2-methoxy-N-(3-(pyridin-4-yl)isoxazol-5-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With pyridine; dmap; In water; at 90.0℃; b) 5-Ethyl-2-methoxy-N-(3-(pyridin-4-yl)isoxazol-5-yl)benzenesulfonamide, 85 To a solution of <strong>[19790-96-6]3-(pyridin-4-yl)isoxazol-5-amine</strong> A15 (50 mg, 0.31 mmol) in pyridine (2 ml.) was added 5-ethyl-2-methoxybenzenesulfonyl chloride 119 (109 mg, 0.46 mmol) and DMAP (4 mg, 0.031 mmol) and the mixture was heated at 90 C overnight. Water (20 ml.) was added and the mixture and adjusted to pH 5-6 with 2 M aqueous HCI and extracted with EtOAc (30 ml. x 3). The combined organic extracts were washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by prep. TLC (DCM/MeOH = 80/1) to give the title compound (15 mg, 13%) as a yellow solid. LCMS-B (ES-API): Rt 2.1 1 min; m/z 360.0 [M+H]+. 1H NMR (400 MHz, DMSO-de) d 8.69 (d, J = 6.0 Hz, 2H), 7.78 (d, J = 6.4 Hz, 2H), 7.71 (d, J = 2.3 Hz, 1H), 7.47 (dd, J = 8.5, 2.3 Hz,1H), 7.14 (d, J = 8.5 Hz, 1H), 6.35 (s, 1H), 3.79 (s, 3H), 2.60 (q, J = 7.6 Hz, 2H), 1.14 (t, J = 7.6 Hz, 3H).
  • 7
  • [ 88040-88-4 ]
  • 3-(3-methoxyphenyl)-1,2-oxazol-5-amine [ No CAS ]
  • 5-ethyl-2-methoxy-N-(3-(3-methoxyphenyl)isoxazol-5-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With pyridine; dmap at 90℃; 86.c c) 5-Ethyl-2-methoxy-N-(3-(3-methoxyphenyl)isoxazol-5-yl)benzenesulfonamide, 86 To a solution of 3-(3-methoxyphenyl)isoxazol-5-amine A17 (250 mg, 1.31 mmol) in pyridine (20 mL) was added 5-ethyl-2-methoxybenzenesulfonyl chloride 119 (461 mg, 1.97 mmol) and DMAP (16 mg, 0.131 mmol) and the mixture was heated at 90 °C overnight. The mixture was diluted with water, adjusted to pH 5 with 1 M aqueous HCI and extracted with EtOAc (40 mL x 3). The combined organic extracts were washed with brine, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Pet. ether/EtOAc= 10/1 to 6/1 to 3/1) to give the title compound (90 mg, 17%) as a white solid. LCMS-B (ES-API): Rt 2.82 min; m/z 389.0 [M+H]+. 1H NMR (400 MHz, DMSO-de) d 7.72 (d, J = 2.3 Hz, 1H), 7.49 (dd, J = 8.5, 2.3 Hz,1H), 7.40 - 7.31 (m, 2H), 7.30 - 7.27 (m, 1H), 7.16 (d, J = 8.6 Hz, 1H), 7.06 - 7.01 (m, 1H), 6.28 (s, 1H), 3.82 (s, 3H), 3.79 (s, 3H), 2.60 (q, J = 7.5 Hz, 2H), 1.14 (t, J = 7.5 Hz, 3H).
  • 8
  • [ 88040-88-4 ]
  • 5-(2-fluorophenyl)isoxazol-3-amine [ No CAS ]
  • 5-ethyl-N-(5-(2-fluorophenyl)isoxazol-3-yl)-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
5% With pyridine In water at 100℃; for 2h; Irradiation; Microwave irradiation; 59 Example 59: 5-Ethyl-N-(5-(2-fluorophenyl)isoxazol-3-yl)-2- methoxybenzenesulfonamide, 59 A solution of 5-ethyl-2-methoxybenzene-1 -sulfonyl chloride 119 (263 mg, 1.12 mmol) and 5- (2-fluorophenyl)isoxazol-3-amine (200 mg, 1.12 mmol) in pyridine (2.0 mL) was irradiated in the microwave at 100 °C for 2 hours. Upon cooling the reaction mixture was added to water (50 mL) and the resultant green solid removed by filtration, the solid was dissolved in a minimum amount of acetone (~4 mL) before petroleum spirits 40-60 °C (70 mL) was added causing dark blue droplets of oil to form. The mother liquor was decanted off and evaporated to yield a tan solid. The solid was dissolved in acetone (2 mL) then petroleum spirits 40-60 °C (50 mL) was added causing a precipitate to form. The solid was removed by filtration and air dried to yield the product as a tan solid (23 mg, 5%). 1H NMR (400 MHz, DMSO-d6) d = 1 1.46 (s, 1H), 7.87 (td, J = 7.7, 1.7, 1H), 7.69 (d, J = 2.3, 1H), 7.66 - 7.55 (m, 1H), 7.52 - 7.33 (m, 3H), 7.15 (d, J = 8.5, 1H), 6.65 (d, J = 3.5, 1H), 3.79 (s, 3H), 2.62 (q, J = 7.6, 2H), 1.15 (t, J = 7.6, 3H). LCMS: Rt 3.787 min, m/z = 377.2 [M+H]+.
  • 9
  • [ 88040-88-4 ]
  • 3-(2-bromophenyl)-1,2-oxazol-5-amine [ No CAS ]
  • N-(3-(2-bromophenyl)isoxazol-5-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With pyridine at 20℃; for 16h; 74 Example 74: N-(3-(2-bromophenyl)isoxazol-5-yl)-5-ethyl-2- methoxybenzenesulfonamide, 74 A mixture of 5-ethyl-2-methoxylbenzenesulfonyl chloride 119 (0.098 g, 0.418 mmol), pyridine (1 ml.) and 3-(2-bromophenyl)-1,2-oxazol-5-amine (0.050 g, 0.209 mmol) was stirred at room temperature for 16 h. The mixtures were diluted with DCM (1 ml.) and washed with 1 M HCI (2 ml_). The aqueous layer was removed and the organic layer was dried to give the crude residue. The product was purified by HPLC to give the title compound 74 (12 mg, 13 % yield). LCMS Rt 5.75 min, m/z = 436.9/438.8 [M+H]+.
  • 10
  • [ 119162-52-6 ]
  • [ 88040-88-4 ]
  • N-(3-(3-bromophenyl)isoxazol-5-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With pyridine at 20℃; for 16h; 75 Example 75: N-(3-(3-bromophenyl)isoxazol-5-yl)-5-ethyl-2- methoxybenzenesulfonamide, 75 A mixture of 5-ethyl-2-methoxylbenzenesulfonyl chloride 119 (0.098 g, 0.418 mmol), pyridine (1 ml.) and 3-(3-bromophenyl)isoxazol-5-amine (0.050 g, 0.209 mmol) was stirred at room temperature for 16 h. The mixtures were diluted with DCM (1 ml.) and washed with 1 M HCI (2 ml_). The aqueous layer was removed and the organic layer was dried to give the crude residue. The product was purified by HPLC to give the title compound (12 mg, 13% yield). LCMS Rt 5.91 min, m/z = 438.8 [M+H]+.
  • 11
  • [ 88040-88-4 ]
  • [ 60135-71-9 ]
  • N-(5-(3,4-dimethoxyphenyl)-1,3,4-oxadlazol-2-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With pyridine at 110℃; for 2h; Irradiation; Microwave irradiation; 125 Example 125 : N-(5-(3,4-Dimethoxyphenyl)-1,3,4-oxadlazol-2-yl)-5-ethyl-2- methoxybenzenesulfonamide, 125 A suspension of 5-ethyl-2-methoxybenzene-1 -sulfonyl chloride 119 (150 mg, 0.639 mmol) and 5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazol-2-amine (141 mg, 0.639 mmol) in pyridine (2 ml.) was irradiated in the microwave at 1 10 °C for 2 hours. The product was purified by column chromatography (0-100% EtOAc in petroleum benzine 40-60 °C) to give the title compound as a white solid (109 mg, 40%). LCMS-C: Rt 6.167 min; m/z 420.1 [M+H]+. 1H NMR (400 MHz, DMSO-de) d 7.70 (d, J = 2.3 Hz, 1H), 7.46 - 7.38 (m, 2H), 7.31 (d, J = 2.0 Hz, 1H), 7.18 - 7.06 (m, 2H), 3.91 - 3.78 (m, 6H), 3.72 (s, 3H), 2.63 (q, J = 7.6 Hz, 2H), 1.18 (t, J = 7.5 Hz, 3H).
  • 12
  • [ 88040-88-4 ]
  • [ 1612-76-6 ]
  • 5-ethyl-2-methoxy-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With pyridine at 110℃; for 2h; Irradiation; Microwave irradiation; 126 Example 126: 5-Ethyl-2-methoxy-N-(5-phenyl-1,3,4-oxadiazol-2- yl)benzenesulfonamide, 126 A suspension of 5-ethyl-2-methoxybenzene-1-sulfonyl chloride 119 (150 mg, 0.639 mmol) and 5-phenyl-1,3,4-oxadiazol-2-amine (103 mg, 0.639 mmol) in pyridine (2 mL) was irradiated in the microwave at 110 °C for 2 hours. The product was purified by column chromatography (0-100% EtOAc in petroleum benzine 40-60 °C) to give the title compound as a white solid (142 mg, 62%). LCMS-C: Rt 6.308 min; m/z 360.1 [M+H]+. 1H NMR (400 MHz, DMSO-de) d 7.88 - 7.80 (m, 2H), 7.71 (d, J = 2.3 Hz, 1H), 7.68 - 7.55 (m, 3H), 7.42 (dd, J = 8.4, 2.3 Hz, 1H), 7.10 (d, J = 8.5 Hz, 1H), 3.72 (s, 2H), 2.63 (q, J = 7.6 Hz, 2H), 1.18 (t, J = 7.6 Hz, 3H).
  • 13
  • [ 2002-03-1 ]
  • [ 88040-88-4 ]
  • 5-ethyl-2-methoxy-N-(5-phenyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 110℃; for 2h; Microwave irradiation; 52 General Method D: (0887) (0888) A suspension of 5-ethyl-2-methoxybenzene-1-sulfonyl chloride 119 (150 mg, 0.639 mmol) and the appropriate amine (0.639 mmol) in pyridine (2 ml.) was irradiated in the microwave at 110 °C for 2 hours. Water (20 ml.) was added and the resultant solid removed by filtration and air-dried to yield the product. (0889) Compounds in Table D were synthesized following analogous methods to general method D:
  • 14
  • [ 88040-88-4 ]
  • 5-(2-methoxyphenyl)isoxazol-3-amine [ No CAS ]
  • 5-ethyl-2-methoxy-N-(5-(2-methoxyphenyl)isoxazol-3-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With pyridine at 100℃; for 2h; Irradiation; Microwave irradiation; 58 Example 58: 5-Ethyl-2-methoxy-N-(5-(2-methoxyphenyl)isoxazol-3-yl) benzenesulfonamide, 58 A solution of 5-(2-methoxyphenyl)isoxazol-3-amine I2 (100 mg, 0.526 mmol) and the 5- ethyl-2-methoxybenzenesulfonyl chloride 119 (123 mg, 0.526 mmol) in pyridine (2 mL) was irradiated in the microwave for 2 h at 100 °C. Upon cooling, the reaction mixture was diluted with water (100 mL) and the resultant precipitate removed by filtration. The solid was washed with water (50 mL), petroleum benzine 40-60 °C (50 mL) and air dried to yield the product 58 as a white solid (97 mg, 47%). 1H NMR (400 MHz, DMSO -d6) d = 1 1.32 (s, 1H), 7.76 (dd, J = 7.8, 1.7, 1H), 7.70 (d, J = 2.3, 1H), 7.53 - 7.45 (m, 2H), 7.21 (d, J = 7.9, 1H), 7.14 (d, J = 8.5, 1H), 7.1 1 - 7.04 (m, 1H), 6.66 (s, 1H), 3.92 (s, 3H), 3.80 (s, 3H), 2.62 (q, J = 7.6, 2H), 1.16 (t, J = 7.6, 3H). LCMS: Rt 6.554 min, m/z 389.1 [M+H]+.
  • 15
  • [ 88040-88-4 ]
  • N-(4-chloro-5-ethylbenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 90 °C / Inert atmosphere
  • 16
  • [ 88040-88-4 ]
  • N-(4-chloro-5-cyclopropylbenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 90 °C / Inert atmosphere
  • 17
  • [ 88040-88-4 ]
  • [ 73498-24-5 ]
  • N-(5-chlorobenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% With pyridine; potassium hydroxide In water at 20 - 110℃; for 6h; Microwave irradiation; 150.b b) N-(5-chlorobenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide 150 b) N-(5-chlorobenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide 150 A suspension of 5-ethyl-2-methoxybenzene-1-sulfonyl chloride (150 mg, 0.639 mmol) and 5-chlorobenzo[d]isoxazol-3-amine A1 (108 mg, 0.639 mmol) in pyridine (1.5 ml.) was irradiated in the microwave at 110 °C for 2 hours. A 10 M aqueous solution of KOH (1 ml.) was added and the resultant mixture was stirred for 4 hours at room temperature. The reaction mixture was loaded onto silica gel and the product purified by column chromatography (0-100% EtOAc in petroleum benzine 40-60 °C) to yield the title compound as a white solid (53 mg, 23%). 1H NMR (400 MHz, DMSO -de) d = 8.1 1 (t, J = 1.4, 1H), 7.71 (d, J = 2.3, 1H), 7.68 (d, J = 1.4, 2H), 7.48 (dd, J = 8.5, 2.3, 1H), 7.10 (d, J = 8.6, 1H), 3.72 (s, 3H), 2.62 (q, J = 7.6, 2H), 1.16 (t, J = 7.6, 3H). LCMS-A: rt 6.637 min; m/z 367.0 [M+H]+.
  • 18
  • [ 88040-88-4 ]
  • 7-fluoro-3-amino-1,2-benzisoxazole [ No CAS ]
  • 5-ethyl-N-(7-fluorobenzo[d]isoxazol-3-yl)-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With pyridine at 100℃; for 2h; Microwave irradiation; 152.b b) 5-Ethyl-N-(7-fluorobenzo[d]isoxazol-3-yl)-2-methoxybenzenesulfonamide 152 b) 5-Ethyl-N-(7-fluorobenzo[d]isoxazol-3-yl)-2-methoxybenzenesulfonamide 152 A solution of 7-fluorobenzo[d]isoxazol-3-amine A3 (100 mg, 0.657 mmol) and 2- methoxy-5-ethylsulfonyl chloride I112 (154 mg, 0.657 mmol) in pyridine (2 mL) was irradiated in the microwave for 2 hours at 100 °C. Upon cooling, the reaction mixture was loaded onto silica gel and purified by column chromatography (Biotage Isolera, 24g S1O2 cartridge, 0-100% EtOAc in petroleum benzine 40-60 °C) to yield the title compound as a white solid (127 mg, 55%). 1H NMR (400 MHz, DMSO-cfe) d = 7.91 (dd, J=8.1, 0.8, 1H), 7.73 (d, J= 2.3, 1H), 7.57 (dd, J 1.9, 8.0, 1H), 7.48 (dd, J=8.5, 2.3, 1H), 7.38 (td, J= 8.0, 4.1, 1H), 7.10 (d, J=8.6, 1H), 3.73 (s, 3H), 2.63 (q, J= 7.6, 2H), 1.16 (t, J= 7.6, 3H). LCMS-A: rt 6.429 min, m/z 351.1 [M+H]+.
  • 19
  • [ 88040-88-4 ]
  • 4-chloro-5-methylbenzo[d]isoxazol-3-amine [ No CAS ]
  • N-(4-chloro-5-methylbenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With pyridine at 100℃; for 2h; Microwave irradiation; 153.b b) N-(4-Chloro-5-methylbenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide 153 b) N-(4-Chloro-5-methylbenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide 153 A solution of 4-chloro-5-methylbenzo[d]isoxazol-3-amine A4 (100 mg, 0.548 mmol) and 2-methoxy-5-ethylsulfonyl chloride I112 (129 mg, 0.548 mmol) in pyridine (2 ml.) was irradiated in the microwave for 2 hours at 100 °C. Upon cooling, the reaction mixture was added to water, the precipitate was removed by filtration and the filtrate was loaded onto silica gel and purified by column chromatography (Biotage Isolera, 24g S1O2 cartridge, 0-100% EtOAc in petroleum benzine 40-60 °C) to give the title compound as a white solid (33 mg, 16%). 1H NMR (400 MHz, DMSO -cfe) d = 10.48 (s, 1H), 7.69 - 7.57 (m, 3H), 7.48 (dd, J=8.5, 2.3, 1H), 7.15 (d, J=8.5, 1H), 3.68 (s, 3H), 2.60 (q, J= 7.5, 2H), 2.42 (s, 3H), 1.15 (t, J= 7.6, 3H). LCMS-A: rt 6.665 min, m/z 381.1 [M+H]+.
  • 20
  • 4-chlorobenzo[d]isoxazol-3-amine [ No CAS ]
  • [ 88040-88-4 ]
  • N-(4-chlorobenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With pyridine at 30℃; for 40h; Inert atmosphere; 154 Example 154: N-(4-chlorobenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide 154 Example 154: N-(4-chlorobenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide 154 A mixture of 5-ethyl-2-methoxybenzenesulfonyl chloride I112 (0.414 g, 1.77 mmol) and 4-chlorobenzo[d]isoxazol-3-amine (0.225 g, 1.34 mmol) in pyridine (2.0 ml.) was stirred at 30 °C for 40 hours under a nitrogen atmosphere. The reaction was concentrated, then sonicated for 2 hours with aqueous HCI (5%) and the resulting precipitate collected. The precipitate was purified using silica gel column chromatography (0-100% ethyl acetate/petroleum benzine 40-60 °C) [189] to give the title compound as two fractions (A and B) with a combined yield of 0.060 g, 12% yield. Fraction A: Yield 0.038 g. 1H NMR (400 MHz, aceton e-cfe) d 8.88 (br s, 1H), 7.75 (d, J = 2.3 Hz, 1H), 7.66 (dd, J = 8.5, 7.6 Hz, 1H), 7.57 (dd, J = 8.5, 0.6 Hz, 1H), 7.49 (dd, J = 8.5, 2.3 Hz, 1H), 7.42 (dd, J = 7.6, 0.6 Hz, 1H), 7.14 (d, J = 8.5 Hz, 1H), 3.91 (s, 3H), 2.66 (q, J = 7.6 Hz, 2H), 1.21 (t, J = 7.6 Hz, 3H). LCMS-B: rt 3.766 min; m/z 367.1/369.1 [M+H]+. Fraction B: Yield 0.021 g. 1H NMR (400 MHz, aceton e-cfe) d 8.88 (br s, 1H), 7.75 (d, J = 2.3 Hz, 1H), 7.65 (dd, J = 8.5, 7.6 Hz, 1H), 7.59 - 7.55 (m, 1H), 7.49 (dd, J = 8.5, 2.3 Hz, 1H), 7.44 - 7.40 (m, 1H), 7.14 (d, J = 8.5 Hz, 1H), 3.90 (s, 3H), 2.66 (q, J = 7.6 Hz, 2H), 1.21 (t, J = 7.6 Hz, 3H). LCMS-B: rt 3.755 min; m/z 367.1/369.1 [M+H]+
  • 21
  • [ 36216-80-5 ]
  • [ 88040-88-4 ]
  • N-(benzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 20℃; for 16h; A mixture of <strong>[36216-80-5]benzo[d]isoxazol-3-amine</strong> and a sulfonyl chloride in pyridine (0.5 ml.) was stirred at room temperature for 16 hours. The reaction was concentrated and diluted with 5% aqueous HCI (1 ml.) and sonicated for a minimum of 30 minutes. The resulting precipitate was collected by filtration and a portion of the crude material (50 mg or less) was purified by mass directed preparative HPLC to give the desired product. See Table B for reaction components and amounts used.
  • 22
  • [ 88040-88-4 ]
  • 5-bromo-4-chlorobenzo[d]isoxazol-3-amine [ No CAS ]
  • N-(5-bromo-4-chlorobenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-bromo-4-chlorobenzo[d]isoxazol-3-amine With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: 5-ethyl-2-methoxybenzene sulfonyl chloride In tetrahydrofuran at -78 - 20℃; 108 Method FD Method FD To a solution of the amine (0.5 mmol, 1.0 eq.) in anhydrous THF (10 ml.) at -78 °C under N2 was added KHMDS (1 M solution in THF, equivalents specified in Table F) dropwise and the mixture was stirred at -78 °C or 0 °C for 30 min to 1 h (specified in Table F). A solution of the sulfonyl chloride (equivalents specified in Tabel F) in anhydrous THF (2.0 ml.) was then added dropwise and the mixture was allowed to warm to RT and stirred overnight. Water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography or prep. TLC to give the title compound.
  • 23
  • [ 88040-88-4 ]
  • 5-bromo-4-methoxybenzo[d]isoxazol-3-amine [ No CAS ]
  • N-(5-cyclopropyl-4-methoxybenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 1.2: 0 - 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 90 °C / Inert atmosphere
  • 24
  • [ 88040-88-4 ]
  • 5-bromo-4-methoxybenzo[d]isoxazol-3-amine [ No CAS ]
  • N-(5-bromo-4-methoxybenzo[d]isoxaz ol-3-yl)-5-ethyl-2-methoxybenzenesulfon amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-bromo-4-methoxybenzo[d]isoxazol-3-amine With potassium hexamethylsilazane In tetrahydrofuran at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: 5-ethyl-2-methoxybenzene sulfonyl chloride In tetrahydrofuran at 0 - 20℃; 108 Method FD Method FD To a solution of the amine (0.5 mmol, 1.0 eq.) in anhydrous THF (10 ml.) at -78 °C under N2 was added KHMDS (1 M solution in THF, equivalents specified in Table F) dropwise and the mixture was stirred at -78 °C or 0 °C for 30 min to 1 h (specified in Table F). A solution of the sulfonyl chloride (equivalents specified in Tabel F) in anhydrous THF (2.0 ml.) was then added dropwise and the mixture was allowed to warm to RT and stirred overnight. Water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography or prep. TLC to give the title compound.
  • 25
  • [ 88040-88-4 ]
  • 5-ethoxybenzo[d]isoxazol-3-amine [ No CAS ]
  • N-(5-ethoxybenzo[d]isoxazol-3-yl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 100℃; Inert atmosphere; 109 Method FB Method FB To a solution of the amine (0.3 mmol, 1.0 eq.) in pyridine (5 ml.) under N2 was added the sulfonyl chloride (2.0 eq.) and the mixture was heated at 100 °C overnight. The reaction was quenched with 1 M aq. HCI, water was then added and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography or prep. TLC to give the title compound. Variations to above conditions have been noted in Table F.
  • 26
  • [ 1437316-91-0 ]
  • [ 88040-88-4 ]
  • N-(2,4-difluoro-3-iodophenyl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
212 mg With pyridine at 20℃; 1 Step-1: Synthesis of N-(2,4-difluoro-3-iodophenyl)-5-ethyl-2- methoxybenzenesulfonamide. To a stirred solution of 2,4-difluoro-3-iodoaniline (200 mg, 0.7843 mmol. 1.0 equiv.) in pyridine (2.0 mL) at room temperature was added 5-ethyl-2-methoxybenzene-l- sulfonyl chloride (184.07 mg, 0.7843 mmol. 1.0 equiv.) The resultant reaction mixture was stirred at room temperature for overnight. The progress of reaction was monitored by TLC. After completion of the reaction, ice cold water was added to reaction mixture. The precipitate formed was filtered using Buchner funnel and washed the product with IN HC1 to remove pyridine. This material was used to next reaction without further purification (212 mg).
  • 27
  • [ 88040-88-4 ]
  • N-(6-(3-(5-ethyl-2-methoxyphenylsulfonamido)-2,6-difluorophenyl)quinazolin-2-yl)pivalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 20 °C 2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 100 °C
  • 28
  • [ 88040-88-4 ]
  • N-(3-(2-aminoquinazolin-6-yl)-2,4-difluorophenyl)-5-ethyl-2-methoxybenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / 20 °C 2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 100 °C 3: sodium hydroxide; ethanol / 3 h / 90 °C
Same Skeleton Products
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