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Chemical Structure| 7516-60-1 Chemical Structure| 7516-60-1

Structure of 7516-60-1

Chemical Structure| 7516-60-1

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Product Details of [ 7516-60-1 ]

CAS No. :7516-60-1
Formula : C7H4Cl2O3S
M.W : 239.08
SMILES Code : O=C(Cl)C1=CC=C(S(=O)(Cl)=O)C=C1
MDL No. :MFCD11169646

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Application In Synthesis of [ 7516-60-1 ]

* 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 [ 7516-60-1 ]

[ 7516-60-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 52537-00-5 ]
  • [ 7516-60-1 ]
  • 4-Br-2-[C(O)O-Wang resin]-aniline [ No CAS ]
  • 5-bromo-2-({4-[(6-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]benzoyl}amino)benzoic acid [ No CAS ]
  • 2
  • [ 508177-67-1 ]
  • [ 7516-60-1 ]
  • [ 859164-85-5 ]
YieldReaction ConditionsOperation in experiment
28% With dmap; triethylamine; In tetrahydrofuran; at -78 - 20℃; for 6h; Preparation 99; 4- (4-Fluoro-3-methox-bvlcarbamovl)-benzenesulfonvl chloride; Dissolve 4-chlorosulfonyl-benzoyl chloride (3.18g, 13. 3mmol) in THF (25mL) and cool to-78C. Slowly add a pre-mixed solution of 4-fluoro-3-methoxybenzyl-amine (1. 91g, 12.3mmol), Et3N (1.64 mL, 11. 8mmol), and DMAP (150mg, 1.23mmol) in THF (25mL) to the above cooled solution over lh. Stir the resulting mixture at-78C for lh, then warm to RT and stir for 4h. Remove all solids by filtration and wash with THF (5mL). Concentrae the filtrate and re-dissolve the crude material in EtOAc (30mL) and wash with 1N HC1 (30mL). Separate the organic and aqueous layers and extract the aqueous phase with additional EtOAc (30mL). Combine the organic solutions dry, filter, and concentrate. Purify the crude material by flash chromatography, using a linear gradient of 100% hexanes to 40% EtOAc/hexanes) to give the title compound as a white solid (1.36g, 28%). MS (ES-) 356.1 (M-1)-. lH NMR (400MHz, CDC13) : 6 8. 11 (d, 2H, J = 8.3), 8.00 (d, 2H, J= 8.8), 7.05 (dd, 1H, J= 8.2, 11. 1), 6.96 (dd, 1H, J= 1. 9,8. 0), 6.86 (m, 1H), 6.44 (br s, 1H), 4.61 (d, 2H, J= 5.7), 3. 88 (s, 3H).
  • 3
  • [ 72320-38-8 ]
  • [ 50595-15-8 ]
  • [ 7516-60-1 ]
  • 3-azidopropyl 4-((2-(tert-butoxy)-2-oxoethoxy)sulfonyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% To a 20 mL reaction vial with magnetic stir bar was massed 4- chlorosulfonylbenzoyl chloride (See procedure above; SI-3, limiting reagent, 0.501 g, 2.10 mmol), and the vial was capped with a septum and positive pressure nitrogen line. Through the septum was added tetrahydrofuran (20 mL/g, 10 mL), and the vial was cooled in a dry ice/acetone bath. Upon equilibrating to temperature, triethylamine (2.0 eq, 0.58 mL, 4.2 mmol) was added in one portion, followed by 3-azidopropan-1-ol (1.0 eq, 0.219 grams, 0.20 mL, 2.09 mmol). The vial was allowed to react in the cooling bath. After one hour, complete conversion was observed (reaction progress monitored by HPLC), and <strong>[50595-15-8]tert-butyl glycolate</strong> (1.5 eq, 0.415 g, 3.14 mmol), and the cooling bath was removed and the vial was allowed to warm to room temperature. After one hour, conversion was observed to be 24percent, and the reaction was allowed to stir overnight at room temperature to reach completion. The crude reaction was diluted in ethyl acetate (40 mL/g, 20 mL), washed twice with water (20 mL/g each, 10 mL each), and finally brine (10 mL/g, 5 mL). The rich organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The oil thus obtained was purified by column chromatography (silica, heptane/ethyl acetate). SI-5 was obtained after concentration as a solid with a yield of 63percent (526 mg). The structure was confirmed with HSQC and HMBC spectroscopy; correlation was observed between the azidopropyl methylene and the carboxylate carbon, confirming connectivity. SI-5: 1H NMR (500 MHz, CDCl3) delta 8.22 (d, J = 7.9 Hz, 2H), 8.04 (d, J = 8.2 Hz, 2H), 4.55 (s, 2H), 4.48 (t, J = 6.1 Hz, 2H), 3.50 (t, J = 6.4 Hz, 2H), 2.08 (quintet, J = 6.3 Hz, 2H), 1.43 (s, 9H) ppm; 13C NMR (126 MHz, CDCl3) delta 164.7, 164.6, 140.0, 134.9, 130.3, 128.1, 83.6, 65.5, 62.8, 48.2, 28.1, 27.9 ppm; HRMS (ESI-TOF): calc?d for
 

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