Category: 127-77-5

Application of 127-77-5, A common heterocyclic compound, 127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, molecular formula is C12H12N2O2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: N1,N3-bis(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)malonamide (1). 5f (253 mg, 1 mmol) was dissolved in the solutionof THF (10 mL) and pyridine (1 mL) before 2a (240 mg, 2 mmol)wasdropwise added. Then the reaction mixture was stirred at roomtemperature overnight until the white solid was precipitated. Thecrude product was filtered and recrystallized with ethanol to give a1 as a light-yellow solid, yield 72%

The synthetic route of 127-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Lei; Li, Li; Zhou, Zi-Han; Jiang, Zheng-Yu; You, Qi-Dong; Xu, Xiao-Li; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 63 – 73;,
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127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C12H12N2O2S

To a suspension of 2,4-bis(methylthio)pyrido[4,3-d]pyrimidin-5(6H)-one (150 mg, 0.627 mmol) in isopropanol (4 mL) were added 4-amino-N-phenylbenzenesulfonamide (327 mg, 1.316 mmol) and 2 drops of conc. HCl, and the reaction mixture was stirred at reflux for 10 hours. The reaction mixture was cooled, diluted with MeOH (10 mL) and treated with aqueous NaHCO3 solution to adjust pH to 7. The precipitate was collected by filtration and washed with water, and purified using column chromatography (silica gel, 0 to 80% 3:1 DCM:MeOH/DCM) to give 190 mg of product as a pale brown solid. MS (ES) m/z = 440.2 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta ppm 2.53 (s, 3H), 6.36 (d, J = 7.34 Hz, 1H), 7.01 – 7.16 (m, 3H), 7.20 – 7.28 (m, 2H), 7.60 (d, J = 7.34 Hz, 1H), 7.73 – 7.81 (m, 2H), 7.86 – 7.99 (m, 2H), 10.20 (br.s, 1H), 12.00 (br s, 1H), 12.25 (s, 1H); 13C NMR (101 MHz, DMSO-d6) delta ppm 14.22, 101.22, 105.88, 120.57, 121.12, 124.49, 128.44, 129.60, 134.23, 138.24, 138.31, 142.32, 158.91, 160.38, 163.83, 174.65. HRMS m/z calculated for C20H18N5O3S2 [M + H+]: 440.0851, found 440.0856.

The synthetic route of 127-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tian, Xinrong; Suarez, Dominic P.; Li, William Hoi Hong; McSherry, Allison K.; Sanchez, Robert M.; Moore, Michael L.; Axten, Jeffrey M.; Tetrahedron Letters; vol. 60; 49; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, molecular formula is C12H12N2O2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: 4-Amino-N-phenylbenzenesulfonamide

Triethylamine (0.07 mL, 0.5 mmol) and phenyl isothiocyanate (2.1 mL, 11 mmol) were added sequentially to a solution of 4 (2.48 g, 10 mmol) in dry THF (10 mL). After heating under reflux for 48 h, all volatiles were removed under vacuum, and the resulting crude material was purified by flash chromatography on silica gel (hexanes/acetone, 3:1) to afford N-phenyl-4-[[(phenylamino)thioxomethyl]amino]benzenesulfonamide (5, also called LED209) (1.34 g, 35%) as a white solid, mp 160-162C. 1H NMR (CD3COCD3, 300 MHz) delta 9.35 (br s, 1H), 9.30 (br s, 1H), 8.98 (br s, 1H), 7.80-7.72 (m, 4H), 7.51-7.47 (m, 2H), 7.38-7.33 (m, 2H), 7.28-7.16 (m, 5H), 7.08-7.04 (m, 1H); 13C NMR (CD3COCD3, 75 MHz) delta 180.2, 143.9, 138.9, 138.2, 135.2, 129.3 (2C), 129.1 (2C), 127.9 (2C), 125.8, 124.6 (3C), 122.8 (2C), 120.8 (2C). Compound 27 was prepared in a similar manner as compound 3 in 90% yield; 1H NMR (CD3COCD3, 300 MHz) delta 9.63 (br s, 1H), 7.80-7.77 (m, 2H), 7.46-7.42 (m, 2H), 7.35-7.27 (m, 3H), 7.15-7.12 (m, 2H), 3.17 (s, 3H), 2.14 (s, 3H). Compound 8 was prepared in a similar manner as compound 4 in 65% yield; 1H NMR (CD3COCD3, 300 MHz) delta7.32-7.13 (m, 7H), 6.68-6.65 (m, 2H), 5.53 (br s, 2H), 3.10 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127-77-5, its application will become more common.

Reference:
Patent; The Board of Regents of The University of Texas System; Omm Scientific, Inc.; SPERANDIO, Vanessa; FALCK, John R.; STEWART, Donald R.; (96 pag.)EP2219635; (2017); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, molecular formula is C12H12N2O2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C12H12N2O2S

To a well-stirred solution of compound 2 (2.48 g, 0.01 mol) inchloroform, benzoyl chloride (1.28 ml, 0.011 mol) in chloroformwas added dropwise at 0 C and stirring was continued in cold condition.After the completion of reaction (monitored by TLC), thereaction mixture was poured into ice cold water. White solid wasfiltered, washed with acetic acid and sodium bicarbonate solutions,dried and purified by recrystallization. Single crystals suitable fordiffraction studies were obtained by slow evaporation fromethanol.Analytical and physical data: Formula: C19H16N2O3S; Yield:70-75%; LCMS (+ve mode): (M + H) = 353.0 (99.5%), RT – 4.349;HRMS: Obtained m/z = 375.0777 (M + Na), cald. = 375.0779.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127-77-5, its application will become more common.

Reference:
Article; Lahtinen, Manu; Kudva, Jyothi; Hegde, Poornima; Bhat, Krishna; Kolehmainen, Erkki; Nonappa; Venkatesh; Naral, Damodara; Journal of Molecular Structure; vol. 1060; 1; (2014); p. 280 – 290;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 127-77-5 as follows. 127-77-5

General procedure: To a solution of the amine 3a-l (1 eq) in anhydrous THF (30 mL/mmol) was added4-nitrophenylisocyanate (1 eq). The reaction mixture was stirred at room temperatureovernight, concentrated. Silica cake was prepared in acetone and chromatographicseparation on silica gel (EtOAc/CH2Cl2 = 1/30 to 1/5) gave the expected compound as asolid. Compounds 4e, 4f, 4h and 4l were further recrystallized in acetone to achieve desiredpurity but with substantially lower yields.

According to the analysis of related databases, 127-77-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Xu; Ahn, Yong-Mo; Lentscher, Adam G.; Lister, Julia S.; Brothers, Robert C.; Kneen, Malea M.; Gerratana, Barbara; Boshoff, Helena I.; Dowd, Cynthia S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4426 – 4430;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

127-77-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 4-chloro-2-(chlorocarbonyl)phenyl benzoate (1 mmol, 1.4 equiv) in DCM (0.2 M), amine (0.7 mmol, 1 equiv) and triethylamine (0.6 mL, 1.2 mmol, 1.7 equiv) were added at 0 C. The mixture was stirred at room temperature (16 h) and extracted with DCM. The organic layer was washed with water and brine, dried (MgSO4), and the solvent was removed under vacuum. The residue was purified by flash column chromatography. (0025) Potassium carbonate (18 mg, 0.13 mmol, 1.2 equiv) was added to a solution of crude product from the previous step (0.11 mmol, 1.0 equiv) in 1:1 MeOH:1,4-dioxane (0.1 M). The reaction mixture was stirred at room temperature (2 h) and acidified with 1 N HCl, followed by extraction with EtOAc and DCM. The organic layer was washed with water and brine, dried (MgSO4), and the solvent was removed under vacuum. The residue was purified by column chromatography (1:19 MeOH:CHCl3), and recrystallized from Et2O/Hex.

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Reference:
Article; Lee, Ill-Young; Gruber, Todd D.; Samuels, Amanda; Yun, Minhan; Nam, Bora; Kang, Minseo; Crowley, Kathryn; Winterroth, Benjamin; Boshoff, Helena I.; Barry III, Clifton E.; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 114 – 126;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics