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Chemical Structure| 16803-92-2 Chemical Structure| 16803-92-2

Structure of 16803-92-2

Chemical Structure| 16803-92-2

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Product Details of [ 16803-92-2 ]

CAS No. :16803-92-2
Formula : C12H11ClN2O2S
M.W : 282.75
SMILES Code : O=S(C1=CC=C(N)C=C1)(NC2=CC=C(Cl)C=C2)=O
MDL No. :MFCD02056459
InChI Key :RBJGYDGKXTYSSL-UHFFFAOYSA-N
Pubchem ID :788021

Safety of [ 16803-92-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 16803-92-2 ]

* 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 [ 16803-92-2 ]

[ 16803-92-2 ] Synthesis Path-Downstream   1~35

  • 4
  • [ 16803-92-2 ]
  • [ 83163-19-3 ]
  • N-(4-Chloro-phenyl)-4-(2-hydroxy-4-methyl-6-p-tolyl-pyrimidin-5-ylazo)-benzenesulfonamide [ No CAS ]
  • 5
  • [ 16803-92-2 ]
  • [ 108-79-2 ]
  • N-(4-Chloro-phenyl)-4-(2-hydroxy-4,6-dimethyl-pyrimidin-5-ylazo)-benzenesulfonamide [ No CAS ]
  • 6
  • [ 16803-92-2 ]
  • N-(4-Chloro-phenyl)-4-hydrazino-benzenesulfonamide [ No CAS ]
  • 7
  • [ 19837-92-4 ]
  • [ 16803-92-2 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride; In water; at 100℃; for 6h; General procedure: A mixture of 0.006 mol of the respective N-(4-(N-arylsulfamoyl)phenyl)acetamide 43a-g in 30 mL of 6 N HCl was kept with stirringunder reflux (100 C) for 6 h. Then, the solution was cooled andneutralized with 20% NaOH. The precipitate formed was vacuumfiltered, washed with water and recrystallized from ethanol/water(1:1).
64% With hydrogenchloride; In acetone; at 20℃; for 0.0833333h;Cooling with ice; General procedure: To a solution of the acetamide 2a-f (1 eq) in EtOH (2 mL/mmol) was added concentratedHCl (1 mL/mmol), the mixture was stirred at 75 C overnight, diluted with water andbasified with 0.2 N NaHCO3 at 0 C to pH = 8. The reaction mixture was filtered andwashed with cold water. The residue was then recrystallized in EtOH and filtered to givethe title compound.
With hydrogenchloride; In ethanol; water; at 75 - 80℃; for 4h; General procedure: Synthesis of the precursor sulfonamides 4a- 4c was achieved bytreating 0.01 mol of substituted aromatic amines (3a-3c) with0.015 mol of 4-(acetylamino)benzene sulfonylchloride (2) in0.03 mol of pyridine at room temperature (RT) for 8 h. Reaction progress was monitored by TLC (with hexane: EtOAc (1:1) mixtureas eluent. Excess pyridine was neutralized with diluted HCl solutionand the product was isolated by filtration. The hydrolysis of theabove product was carried out by refluxing it with concentrated HCl in ethanol for 4 h. The clear solution was cooled and neutralized by ammonium hydroxide solution. The solid precipitated was filtered and dried at 50-55 C (Scheme 1).
With hydrogenchloride; at 100℃; for 2h; General procedure: 3-/4-Acetamidobenzenesulfonyl chloride (1, 1 equiv.) was dissolved in dichloromethane (80mL) at 0C. An appropriate aniline (1.05 equiv.) and triethylamine (2 equiv.) were added to the solution dropwise. Then, the mixture was stirred for 2h at room temperature. TLC monitored reaction progress. After reaction completed, 2N HCl and Brine solution were added to the mixture. The residue was obtained by washing the mixture with water and dichloromethane and the solid recovered by filtration. The compound was added to 12N HCl, heated to reflux and stirred for 2h. Cooled to room temperature, the mixture was washed by NaOH, and extracted with dichloromethane (3×30mL) and methanol (3×30mL). Combined organic layers were dried over magnesium sulfate and concentrated under vacuum. The crude products were purified by a silica-gel column chromatography. 4a [15], 4b [20], 4c [21], 4d [21], 4e [17], 4f [22], 4g [17], 4h [15], 4i [23], 4j [21], 4k [24], 4l [25], 4m [26].

  • 9
  • [ 16803-92-2 ]
  • [ 622-59-3 ]
  • <i>N</i>-(4-chloro-phenyl)-4-(3-<i>p</i>-tolyl-thioureido)-benzenesulfonamide [ No CAS ]
  • 10
  • [ 16803-92-2 ]
  • [ 556-61-6 ]
  • <i>N</i>-(4-chloro-phenyl)-4-(3-methyl-thioureido)-benzenesulfonamide [ No CAS ]
  • 11
  • [ 16937-03-4 ]
  • [ 16803-92-2 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride; tin; In ethanol; water;Reflux; General procedure: Concentrated HCl (10-15 ml) was added slowly to a mixture of 4-nitrobenzenesulfonamide or 4-nitrobenzamide analog (13a-q,1.4 mmol, 1 eq) and Sn granules (2-2.5 eq) in ethanol (10 mL). The reaction mixture was refluxed for 3.5-6 h. When the TLC plates howed that there is no more starting material left, the reaction mixture was cooled down to rt. NaOH (30% or 5M, aq) was added to the mixture until it became basic. The mixture was extracted with EA or DCM and the organic layer was dried with Na2SO4. The solvent was evaporated. The product was purified with column chromatography when required. 4.6.4.25 4-Amino-N-(4-chlorophenyl)benzenesulfonamide (14h) From 13h (1.41 g, 4.5 mmol) with general procedure B. White solid (1.25 g, 98%) that was used without further purification. 1H NMR (DMSO-d6): δ 5.99 (2H, s), 6.53 (2H, d, J = 8.6 Hz), 7.06 (2H, d, J = 8.8 Hz), 7.26 (2H, d, J = 8.8 Hz), 7.37 (2H, d, J = 8.6 Hz), 10.0 (1H, s).
With hydrogenchloride; iron; In methanol; water;pH 2.0;Heating / reflux; To a stirred solution of 4-nitro phenyl sulfonamide 9-2 (300 mg, 0.95mmol) in methanol (10 mL) was added powered Fe (600mg) and the reaction mixture was acidified (pH~2) by using HCl and refluxed overnight. The reaction mixture was filtered, and the filtrate was concentrated under vacuum to give compound 9-3 as a yellow solid (yield: 200 mg). Mass: 286 [M+l].
  • 12
  • [ 16803-92-2 ]
  • [ 124-63-0 ]
  • <i>N</i>-(4-chloro-phenyl)-4-methanesulfonylamino-benzenesulfonamide [ No CAS ]
  • 13
  • [ 16803-92-2 ]
  • [ 1548-13-6 ]
  • N-(4-chloro-phenyl)-4-[3-(4-trifluoromethyl-phenyl)-ureido]-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.2% In toluene; at 40 - 60℃; To a stirred solution of compound 9-3 (150 mg, 0.524 mmol) in toluene (15 mL) was added 4-trifluorophenyl isocyanate (0.07 mL, 0.524mmol) at 40 0C and the reaction mixture was maintained at 60 0C overnight. The solid which precipitated out was filtered, given pet-ether and pentane washings and recrystalised in acetone to give compound 25 as a light brown solid (30 mg, 60.2%); m.p. 252-257 0C; LCMS purity 97.2%; Mass: 432 [M+l]; 1HNMR: (300 MHz; DMSO-D6) δ: 7.63-7.75 (8H, Ar CH); 9.26 (2H, NH).
  • 15
  • [ 121-60-8 ]
  • 4-acetoxy-<i>N</i>1-acetyl-<i>o</i>-phenylenediamine [ No CAS ]
  • [ 16803-92-2 ]
  • 16
  • [ 16803-92-2 ]
  • 4-(3-methyl-5-oxo-2-pyrazolin-1-yl)-N-(4-chlorophenyl)benzenesulfonamide [ No CAS ]
  • 18
  • [ 16803-92-2 ]
  • [ 94011-79-7 ]
  • [ 1167997-44-5 ]
  • 19
  • dimethyl 4-(methoxymethylene)-2-pentenedioate [ No CAS ]
  • [ 16803-92-2 ]
  • [ 1160499-45-5 ]
  • 21
  • [ 117-80-6 ]
  • [ 16803-92-2 ]
  • [ 1241891-85-9 ]
  • 22
  • [ 16803-92-2 ]
  • [ 189894-90-4 ]
  • [ 1228268-32-3 ]
  • 23
  • [ 1227857-41-1 ]
  • [ 16803-92-2 ]
  • [ 1262334-07-5 ]
  • 24
  • [ 18356-30-4 ]
  • [ 16803-92-2 ]
  • [ 1326238-17-8 ]
  • 25
  • [ 18356-30-4 ]
  • [ 16803-92-2 ]
  • [ 1326238-18-9 ]
  • [ 1326238-17-8 ]
  • 26
  • [ 1258977-52-4 ]
  • [ 16803-92-2 ]
  • [ 1258977-80-8 ]
  • 27
  • [ 1258977-53-5 ]
  • [ 16803-92-2 ]
  • [ 1258977-92-2 ]
  • 28
  • [ 70475-59-1 ]
  • [ 16803-92-2 ]
  • [ 1160212-20-3 ]
  • 29
  • [ 46324-06-5 ]
  • [ 16803-92-2 ]
  • C23H17ClN2O4S [ No CAS ]
  • 30
  • [ 46727-01-9 ]
  • [ 16803-92-2 ]
  • C24H21ClN2O6S [ No CAS ]
  • C24H19ClN2O5S [ No CAS ]
  • 31
  • [ 74222-66-5 ]
  • [ 16803-92-2 ]
  • C24H21ClN2O5S [ No CAS ]
  • C24H19ClN2O4S [ No CAS ]
  • 32
  • [ 16803-92-2 ]
  • 3-(2-chlorophenyl)propenoyl chloride [ No CAS ]
  • 3-(2-chlorophenyl)-N-(4-(N-(4-chlorophenyl)sulfamoyl)phenyl)acrylamide [ No CAS ]
  • 33
  • [ 16803-92-2 ]
  • [ 2243-83-6 ]
  • N-(4-(N-(4-chlorophenyl)sulfamoyl)phenyl)-2-naphthamide [ No CAS ]
  • 34
  • 4-fluorocinnamoyl chloride [ No CAS ]
  • [ 16803-92-2 ]
  • N-(4-(N-(4-chlorophenyl)sulfamoyl)phenyl)-3-(4-fluorophenyl)acrylamide [ No CAS ]
  • 35
  • [ 67132-17-6 ]
  • [ 16803-92-2 ]
  • N-((4-(N-(4-chlorophenyl)sulfamoyl)phenyl)carbamothioyl)-[1,1'-biphenyl]-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.55 g In acetone;Reflux; General procedure: 4-Phenylbenzoyl chloride (15, 1.2 mmol, 1-1.2 eq) in acetone (10 mL) was added slowly to a mixture of potassium thiocyanate (1-1.2 eq) in acetone (10 mL). The reaction mixture was refluxed 1.5-3 h and the reaction was monitored by TLC. The reaction mixture was cooled down to rt and an appropriate benzenesulfonamide or benzamide analog (14a-q, 1 eq) in acetone (10 mL) was slowly added. The reaction mixture was refluxed for 2-4 h orovernight. When starting material was disappeared (detected by TLC plate), the mixture was poured on ice cold water which pH was adjusted to 5 with HCl. If the product crystallized, it was filtered and washed with small amount of cold water. Otherwise the mixture was extracted with EA. The product was purified by column chromatography, recrystallization or washing with hexane. 4.6.4.43 N-((4-(N-(4-Chlorophenyl)sulfamoyl)phenyl)carbamothioyl)-[1,1'-biphenyl]-4-carboxamide (17h) From 14h (0.62 g, 2.2 mmol) with general procedure C. White solid (0.55 g, 48%). 1H NMR (DMSO-d6): δ 7.14 (2H, d, J = 8.8 Hz), 7.33 (2H, d, J = 8.8 Hz), 7.45 (1H, t, J = 7.6 Hz), 7.53 (2H, t, J = 7.3 Hz), 7.78 (2H, m), 7.80 (2H, d, J = 8.8 Hz), 7.86 (2H, d, J = 8.8 Hz), 7.98 (2H, d, J = 8.8 Hz), 8.09 (2H, d, J = 8.8 Hz), 10.47 (1H, s), 11.72 (1H, s), 12.76 (1H, s); 13C NMR (DMSO-d6): δ 121.6, 124.2, 126.6, 127.0, 127.4, 128.2, 128.5, 129.1, 129.2, 129.5, 130.7, 136.0, 136.6, 138.7, 142.0, 144.6, 167.7, 179.2; ESI-MS 519.95 [M-H]-; Anal. Calcd for C26H20ClN3O3S2 * 0.3H2O: C 59.21, N 7.97, H 3.94, S 12.16; found: C 58.82, N 7.88, H 3.85, S 12.04.
 

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