Category: 121-30-2

Synthetic Route of 121-30-2, These common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, 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.

To a solution of aminoacetaldehyde dimethylacetal (2.18 mL, 2.13 g, 20.2 mmol) in EtOAc (25 mL) at 0 C. was added dropwise a solution of HCl in ether (13 mL, 2N solution in ether). The mixture was stirred at 0 C. for 5 minutes. To this solution, 4-chloro-6-aminobenzene-1,3-disulfonamide (Aldrich, 5.8 g, 20.3 mmol) in diethylene glycol dimethylether (30 mL) was added. The reaction mixture was then heated at 60-90 C. for 1 hour. The solvent was decanted and the solid was dissolved in water. An aqueous solution of Na2CO3 (10%) was added to adjust the pH 7-8, extracted with EtOAc, dried over Na2SO4, filtered and the solvent was evaporated. The crude material was chromatographed on silica gel eluting with CH2Cl2:EtOAc:MeOH (1:1:0.2 to 1:1:1) to give the title compound (3 g, 53% yield) as a white solid: mp 157-160 C. 1H NMR (400 MHz, d6-DMSO) delta 7.97 (s, 1H), 7.05 (s, 1H), 5.65-4.70 (m, 1H), 2.88-2.96 (m, 1H), 2.77-2.84 (m, 1H); 13C NMR (100 MHz, d6-DMSO) delta 147.1, 134.8, 128.4, 125.9, 118.7, 117.6, 68.1, 44.9. Mass spectrum (API-TIS) m/z 325 (M-H), 327 (MH+); Anal. calcd for C8H11ClN4O4S20: C, 30.06; H, 3.54; N, 16.70. Found: C, 30.26; H, 3.40; N, 16.38.

Statistics shows that 4-Amino-6-chlorobenzene-1,3-disulfonamide is playing an increasingly important role. we look forward to future research findings about 121-30-2.

Reference:
Patent; NitroMed, Inc.; US2006/189603; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 121-30-2, A common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, molecular formula is C6H8ClN3O4S2, 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.

To a solution of 2,4-disulfamyl-5-chloroaniline (15c, 3 g, 10 mmol) in acetonitrile (120 mL) at 40 C was slowly added concd sulfuric acid (13.5 mL). After 30 min, to the solution was added sodium nitrite (1.32 g, 19.1 mmol) portionwise. The solution was stirred at 0 C for 1 h, to which was then added a solution of CuBr2 (2.46 g, 11 mmol) in water (2 mL) in portions. After 1.5 h, the reaction mixture was warmed to room temperature and then heated to 80 C to evolve nitrogen gas. When no further gas was generated, the solution was concentrated. Purification by flash column chromatography on a silica gel column with hexane/EtOAc (1:1) provided a pale yellowish solid 16c in 62% yield. Mp 291-292 C (lit:refPreviewPlaceHolder25 290 C). 1H NMR (400 MHz, acetone-d6) delta 8.67 (s, 1H; ArH), 8.36 (s, 1H; ArH), 7.03 (br, 4 H; SO2NH2). 13C NMR (100 MHz, acetone-d6) delta 145.0, 144.1, 140.7, 134.0, 128.8, 96.7.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Tan, Chen-Ming; Chen, Grace Shiahuy; Chen, Chien-Shu; Chang, Pei-Teh; Chern, Ji-Wang; Bioorganic and Medicinal Chemistry; vol. 19; 21; (2011); p. 6316 – 6328;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 121-30-2, These common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, 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.

To a solution of aminoacetaldehyde dimethylacetal (2.18 mL, 2.13 g, 20.2 mmol) in EtOAc (25 mL) at 0 C. was added dropwise a solution of HCl in ether (13 mL, 2N solution in ether). The mixture was stirred at 0 C. for 5 minutes. To this solution, 4-chloro-6-aminobenzene-1,3-disulfonamide (Aldrich, 5.8 g, 20.3 mmol) in diethylene glycol dimethylether (30 mL) was added. The reaction mixture was then heated at 60-90 C. for 1 hour. The solvent was decanted and the solid was dissolved in water. An aqueous solution of Na2CO3 (10%) was added to adjust the pH 7-8, extracted with EtOAc, dried over Na2SO4, filtered and the solvent was evaporated. The crude material was chromatographed on silica gel eluting with CH2Cl2:EtOAc:MeOH (1:1:0.2 to 1:1:1) to give the title compound (3 g, 53% yield) as a white solid: mp 157-160 C. 1H NMR (400 MHz, d6-DMSO) delta 7.97 (s, 1H), 7.05 (s, 1H), 5.65-4.70 (m, 1H), 2.88-2.96 (m, 1H), 2.77-2.84 (m, 1H); 13C NMR (100 MHz, d6-DMSO) delta 147.1, 134.8, 128.4, 125.9, 118.7, 117.6, 68.1, 44.9. Mass spectrum (API-TIS) m/z 325 (M-H), 327 (MH+); Anal. calcd for C8H11ClN4O4S20: C, 30.06; H, 3.54; N, 16.70. Found: C, 30.26; H, 3.40; N, 16.38.

Statistics shows that 4-Amino-6-chlorobenzene-1,3-disulfonamide is playing an increasingly important role. we look forward to future research findings about 121-30-2.

Reference:
Patent; NitroMed, Inc.; US2006/189603; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 121-30-2,Some common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, molecular formula is C6H8ClN3O4S2, 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.

1 kg of 4-amino-6-chloro-1,3-benzenedisulfonamide was mixed with 10 kg of purified water, stirred and heated to 80 C, and 0.5 kg of formaldehyde was added dropwise, and the addition was completed in about two hours. And reacted at 100 C for 0.5 hour. Cooling to 15 , adding 0.3 kg of sodium hydroxide, 0.07 kg of medicinal charcoal, 60 C stirring for 30 minutes, insulation filter. The filtrate stirring to adjust the pH value of 5.5, cooling down to 20 below the centrifugal dehydration, and with a small amount of purified water leaching, drying wet boutique. After drying crushed and packaged, the product of hydrochlorothiazide.The product was white crystalline powder and was detected by high performance liquid chromatography, which was consistent with the retention time of the main peak of the hydrochlorothiazide standard. The UV spectrum was detected at 273nm and 323nm, and the absorbance at the wavelength of 273nm was the same as that at 323nm The absorbance ratio was 5.7; consistent with the infrared absorption profile of the hydrochlorothiazide standard.The residual methanol in the product does not exceed 0.3%, the ethanol does not exceed 0.5%, the weight loss is not more than 0.5%, the ignition residue does not exceed 0.1%, the pH, chloride, heavy metal and microbial limit are in accordance with the provisions of the Chinese Pharmacopoeia 2010 edition The Calculated according to dry goods, C7H8ClN3O4S2 content of 99.2%.

The synthetic route of 121-30-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anyang Jiuzhou pharmaceutical Co., Ltd; Cao, Junhua; (4 pag.)CN103396381; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, molecular formula is C6H8ClN3O4S2, 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. Recommanded Product: 121-30-2

A suspension of 1000 g (3.5 mol) of 4-Amino-6-chloro-l,3-benzenedisulfonamide Q and 78.9 g (2.63 mol) paraformaldehyde in 1264 ml of methanol was heated to reflux and a solution of 55.56 ml of concentrated sulphuric acid in 180.54 ml of methanol was added to the refluxing reaction mixture. After refluxing for one hour additional 23.34 g (0.78 mol) paraformaldehyde was added. The reaction mass was further refluxed for one hour and one more lot of 13.88 g (0.46 mol) paraformaldehyde was 5 added. The combined reaction mixture was refluxed for six hours followed by cooling to 20-300C. It was further stirred at this temperature for one hour and filtered; the solid mass was washed successively with methanol and water to get 980 g off white crude wet product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 121-30-2, its application will become more common.

Reference:
Patent; UNICHEM LABORATORIES LIMITED; WO2007/26376; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 121-30-2, 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 121-30-2 as follows.

To the product of Example 74a (1.63 g, 10 mmol) and 2-amino-6-chloro-1,3-benzenedisulfonamide (Aldrich Chemical Co.,1.439 g, 5 mmol) in anhydrous dioxane (50 mL) was added Amberlyst (15) wet strongly acidic resin (3 g). The reaction mixture was stirred gently at room temperature for 2 days, then decanted into another flask. The resin was washed with dioxane (2 mL) and the washings added to the reaction mixture. Fresh Amberlyst (15) wet strongly acidic resin (2 g) was added to the reaction mixture and the stirring was continued at room temperature for 24 hours. The resin was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was treated with ethyl acetate and washed with saturated aqueous sodium carbonate, water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by column chromatography over silica gel, eluting with 3% methanol in dichloromethane gave 1.3 g of an oil that was triturated with 20% ethyl acetate in hexane to give the title compound (1.1 g, 54% yield) as a white solid: mp 113-117 C.; 1H NMR (d6-DMSO) delta 8.03 (s, 1H), 8.01 (s, 1H), 7.97 (s, 1H), 7.52 (s, 2H), 6.98 (s, 1H), 4.96-4.89 (m, 1H), 4.77-4.65 (m, 2H), 2.28-2.15 (m, 2H); 13C NMR (d6-DMSO) delta 146.3, 134.2, 128.6, 125.4, 118.2, 117.1, 69.1, 63.3, 30.4. Mass spectrum (API-TIS) m/z 404 (MH)+, 406 (MH+2)+.

According to the analysis of related databases, 121-30-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NitroMed, Inc.; US2006/189603; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics