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[ CAS No. 547739-67-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 547739-67-3
Chemical Structure| 547739-67-3
Chemical Structure| 547739-67-3
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Product Details of [ 547739-67-3 ]

CAS No. :547739-67-3 MDL No. :MFCD23699339
Formula : C8H6Cl2O3S Boiling Point : -
Linear Structure Formula :- InChI Key :BSHLCKNAKRLVSS-UHFFFAOYSA-N
M.W : 253.10 Pubchem ID :20646249
Synonyms :

Safety of [ 547739-67-3 ]

Signal Word:Danger Class:6.1,8
Precautionary Statements:P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501 UN#:2927
Hazard Statements:H301-H311-H314-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 547739-67-3 ]

* 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 [ 547739-67-3 ]

[ 547739-67-3 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 22381-54-0 ]
  • [ 547739-67-3 ]
  • [ 651728-83-5 ]
  • 3
  • [ 99-75-2 ]
  • [ 372198-41-9 ]
  • [ 547739-67-3 ]
YieldReaction ConditionsOperation in experiment
With chlorosulfonic acid In chlorosulfonic acid at 120℃; 1 Synthesis of methyl 3-(chlorosulfonyl)-4-methylbenzoate (1a) Chlorosulfonic acid (6 mL, 90.3 mmol) was added dropwise to melt methyl p-toluate (12.7 g, 84.4 mmol) heated at 120°C. The reaction mixture was stirred at this temperature for 4 hours. After completion of the reaction based on TLC monitoring, the reaction mixture was cooled to room temperature, and diluted in water (200 mL). The solution was extracted with ethyl acetate several times, and organic layer was washed with water and brine, dried in Na2SO4 and concentrated in vacuo to give a mixture of two compounds, which are compound 1a and 3-(chlorosulfonyl)-4-methylbenzoyl chloride. [0120] 1H NMR (CDCl3) δ = 2.9 (s, 3H, CH3); 4.0 (s, 3H, OCH3); 7.55 (d, 1H, H-Ar); 8.3 (d, 1H, H-Ar); 8.7 (s, 1H, H-Ar).
With chlorosulfonic acid In neat liquid at 120℃; 1 Synthesis of methyl 3-(chlorosulfonyl)-4-methylbenzoate (la) Chlorosulfonic acid (6 mL, 90.3 mmol) was added dropwise to melt methyl /?-toluate (12.7 g, 84.4 mmol) heated at 120°C. The reaction mixture was stirred at this temperature for 4 hours. After completion of the reaction based on TLC monitoring, the reaction mixture was cooled to room temperature, and diluted in water (200 mL). The solution was extracted with ethyl acetate several times, and organic layer was washed with water and brine, dried in Na2S04 and concentrated in vacuo to give a mixture of two compounds, which are compound l_a and 3-(chlorosulfonyl)-4-methylbenzoyl chloride. 'H NMR (CDCh) δ = 2.9 (s, 3H, CH3); 4.0 (s, 3H, OCH3); 7.55 (d, 1H, H-Ar); 8.3 (d, 1H, H-Ar); 8.7 (s, 1H, H-Ar).
With chlorosulfonic acid In neat (no solvent) at 120℃; for 4h; Methyl p-toluate (12.7 g, 84.4 mmoles) washeated at 120°C in absence of solvent. When the solid material melted, the chlorosulfonicacid (6 mL, 90 mmoles) was added dropwise. The mixture was stirredat 120°C for 4 hrs, then cooled to room temperature and hydrolysed with 200 mL of cold water. Crude material was extracted with ethyl acetate (3x 75 mL). The organic layers were collected and washed with water and brine,dried with Na2SO4, and concentrated in vacuo. The resulting mixture consisted in a solid in dispersionin oil, containing the unreacted starting material (methyl p-toluate), and the compounds 2and 3. At this point it was notpossible to isolate separately these products. Therefore, this crude materialwas solubilized in a mixture of 100 mL of toluene and 20 mL of brine, andtreated with 50 mL of aqueous HCl (2N) in presence of a catalytic amount (3%)of tetrabutylammonium bromide. The mixture was refluxed overnight and thencooled to room temperature and the two layers were separated cautiously. Theorganic layer was washed twice with water and brine, dried with Na2SO4,and concentrated in vacuo. The crudematerial consisted in a solid in dispersion in oil. Successive cooling to 0°Cand filtration led to compound 2(4.2 g, about 20% yield, contaminated by starting methyl toluate) isolated aswhite solid, and compound 3 as anoil (2.1 g, 10% yield). Compound 2has yet been described in the literature. The 1H NMR spectra and theESI-MS analysis of the white solid containing compound 2 and unreacted methyl p-toluateallowed us to identify unambiguously its presence. Compound 2: 1H NMR(250 MHz, CDCl3) (ppm): 8.70 (s, 1H), 8.34(d, J = 8.5 Hz, 1H), 7.55 (d, J = 8.5 Hz, 1H), 4.10 (s, 3H), 2.90 (s,3H). ESI-MS: m/z calcd for C9H9ClO4S[M+H]+: 248.9 ; found 248.9.
  • 4
  • [ 547739-67-3 ]
  • [ 134-20-3 ]
  • methyl 2-(3-(chlorosulfonyl)-4-methylbenzamido)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 2-carbomethoxyaniline With sodium hydride In tetrahydrofuran for 0.333333h; Stage #2: 3-chlorosulfonyl-4-methylbenzoic acid chloride In tetrahydrofuran at 20℃;
  • 5
  • [ 547739-67-3 ]
  • [ 135484-83-2 ]
  • C16H13BrClNO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-amino-4-bromo-benzoic acid methyl ester With sodium hydride In tetrahydrofuran for 0.333333h; Stage #2: 3-chlorosulfonyl-4-methylbenzoic acid chloride In tetrahydrofuran at 20℃;
  • 6
  • [ 5900-58-3 ]
  • [ 547739-67-3 ]
  • C16H13Cl2NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-amino-4-chloro-benzoic acid methyl ester With sodium hydride In tetrahydrofuran for 0.333333h; Stage #2: 3-chlorosulfonyl-4-methylbenzoic acid chloride In tetrahydrofuran at 20℃;
  • 7
  • [ 5202-89-1 ]
  • [ 547739-67-3 ]
  • C16H13Cl2NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-chlorobenzenesulfonyl chloride With sodium hydride In tetrahydrofuran for 0.333333h; Stage #2: 3-chlorosulfonyl-4-methylbenzoic acid chloride In tetrahydrofuran at 20℃;
  • 8
  • [ 547739-67-3 ]
  • [ 52727-57-8 ]
  • C16H13BrClNO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-bromo-2-aminobenzoic acid methyl ester With sodium hydride In tetrahydrofuran for 0.333333h; Stage #2: 3-chlorosulfonyl-4-methylbenzoic acid chloride In tetrahydrofuran at 20℃;
  • 9
  • [ 547739-67-3 ]
  • [ 2475-81-2 ]
  • C16H13ClFNO5S [ No CAS ]
  • 10
  • [ 547739-67-3 ]
  • [ 319-24-4 ]
  • C16H13ClFNO5S [ No CAS ]
  • 11
  • [ 547739-67-3 ]
  • [ 18595-16-9 ]
  • C17H16ClNO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-amino-5-methylbenzoic acid methyl ester With sodium hydride In tetrahydrofuran for 0.333333h; Stage #2: 3-chlorosulfonyl-4-methylbenzoic acid chloride In tetrahydrofuran at 20℃;
  • 12
  • [ 547739-67-3 ]
  • [ 18595-13-6 ]
  • C17H16ClNO5S [ No CAS ]
  • 13
  • [ 547739-67-3 ]
  • [ 19258-73-2 ]
  • C18H18ClNO5S [ No CAS ]
  • 14
  • [ 1029420-48-1 ]
  • [ 547739-67-3 ]
  • C19H20ClNO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 2-amino-5-isopropylbenzoate With sodium hydride In tetrahydrofuran for 0.333333h; Stage #2: 3-chlorosulfonyl-4-methylbenzoic acid chloride In tetrahydrofuran at 20℃;
  • 15
  • [ 2475-78-7 ]
  • [ 547739-67-3 ]
  • C18H18ClNO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-amino-5-ethylbenzoic acid methyl ester With sodium hydride In tetrahydrofuran for 0.333333h; Stage #2: 3-chlorosulfonyl-4-methylbenzoic acid chloride In tetrahydrofuran at 20℃;
  • 16
  • [ 547739-67-3 ]
  • C21H16ClFN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 17
  • [ 547739-67-3 ]
  • C22H18ClFN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 18
  • [ 547739-67-3 ]
  • 2-(3-(N-(3-chlorophenyl)sulfamoyl)-4-methylbenzamido)-5-fluorobenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 19
  • [ 547739-67-3 ]
  • C22H18ClFN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 20
  • [ 547739-67-3 ]
  • 2-(3-(N-(3-chlorophenyl)sulfamoyl)-4-methylbenzamido)-5-methylbenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 21
  • [ 547739-67-3 ]
  • C23H21ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 22
  • [ 547739-67-3 ]
  • 2-(3-(N-(3-chlorophenyl)sulfamoyl)-4-methylbenzamido)-6-methylbenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 23
  • [ 547739-67-3 ]
  • C23H21ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 24
  • [ 547739-67-3 ]
  • 2-(3-(N-(3-chlorophenyl)sulfamoyl)-4-methylbenzamido)-4,5-dimethylbenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 25
  • [ 547739-67-3 ]
  • C24H23ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 26
  • [ 547739-67-3 ]
  • 4-bromo-2-(3-(N-(3,4-dichlorophenyl)sulfamoyl)-4-methylbenzamido)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 27
  • [ 547739-67-3 ]
  • C22H17BrCl2N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 28
  • [ 547739-67-3 ]
  • C23H21ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 29
  • [ 547739-67-3 ]
  • C24H23ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 30
  • [ 547739-67-3 ]
  • C24H23ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 31
  • [ 547739-67-3 ]
  • C25H25ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 32
  • [ 547739-67-3 ]
  • C25H19ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 33
  • [ 547739-67-3 ]
  • C26H21ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 34
  • [ 547739-67-3 ]
  • C21H15Cl3N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 35
  • [ 547739-67-3 ]
  • C22H17Cl3N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 36
  • [ 547739-67-3 ]
  • C21H15Cl3N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 37
  • [ 547739-67-3 ]
  • C22H17Cl3N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 38
  • [ 547739-67-3 ]
  • 5-bromo-2-(3-(N-(3,4-dichlorophenyl)sulfamoyl)-4-methylbenzamido)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 39
  • [ 547739-67-3 ]
  • C22H17BrCl2N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 40
  • [ 547739-67-3 ]
  • C21H15Cl2FN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 41
  • [ 547739-67-3 ]
  • C22H17Cl2FN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 42
  • [ 547739-67-3 ]
  • C21H15Cl2FN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 43
  • [ 547739-67-3 ]
  • C22H17Cl2FN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 44
  • [ 547739-67-3 ]
  • 2-(3-(N-(3,4-dichlorophenyl)sulfamoyl)-4-methylbenzamido)-5-methylbenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 45
  • [ 547739-67-3 ]
  • C23H20Cl2N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C
  • 46
  • [ 547739-67-3 ]
  • C22H18Cl2N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h 1.2: 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.33 h 2.2: 20 °C 3.1: lithium hydroxide / tetrahydrofuran / 2 h / 55 °C
  • 47
  • [ 547739-67-3 ]
  • [ 21597-54-6 ]
  • C20H16ClNO5S [ No CAS ]
  • 48
  • [ 547739-67-3 ]
  • [ 90928-92-0 ]
  • 2-methyl-5-(((3-methyl-1,2,4-oxadiazol-5-yl)methyl)carbamoyl)benzenesulfonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With 2,6-dimethylpyridine In dichloromethane at 0 - 15℃; for 1h;
  • 49
  • [ 547739-67-3 ]
  • 3-(N-(4-(isoxazol-5-yl)phenyl)sulfamoyl)-4-methyl-N-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 - 15 °C 2: pyridine / tetrahydrofuran / 16 h / 60 °C
  • 50
  • [ 547739-67-3 ]
  • 4-methyl-N-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)-3-(N-(4-(oxazol-5-yl)phenyl)sulfamoyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 - 15 °C 2: pyridine / tetrahydrofuran / 16 h / 60 °C
  • 51
  • [ 547739-67-3 ]
  • [ 613-94-5 ]
  • C15H13ClN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: benzoic acid hydrazide With pyridine In acetonitrile for 0.166667h; Stage #2: 3-chlorosulfonyl-4-methylbenzoic acid chloride In acetonitrile at 20℃; for 1h; 1.4. General procedure 3 (GP3): Synthesis of compounds 2a-e General procedure: A mixture of ArCONHNH2 7 (3 mmol), pyridine (3 mmol) and acetonitrile (10 mL) was added dropwise over 15 min to a solution of the substituted benzoyl chloride 10 (3.05 mmol) in anhydrous acetonitrile (5 mL) at room temperature with vigorous stirring. The mixture was incubated for 1 h under the same conditions. The product was isolated by addition of cold water (100 mL), the precipitate was collected by filtration and was dissolved in 20 mL toluene containing phosphorus oxychloride (0.1 ml) at boiling temperature. After the solution was cooled to room temperature, 0.56 ml phosphorus oxychloride (6 mmol) was slowly added. The reaction mixture was refluxed for 6 h. The hot solution was gently decanted from the oily residue, and the solvent was exchanged for acetonitrile. To the resulting solution of the sulfonyl chloride 12 was added 25% aqueous ammonia to yield a pH of 8-9. The mixture was stirred at 50 °C for 2 h. After cooling, the mixture was poured into 50 mL of ice water. A precipitate formed and was collected by filtration, washed with water and dried at 50 °C. The product was purified by subsequent recrystallization from a mixture of DMF-ethanol-water (3:1:1) to give the title compounds 2a-e.
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