Month: August 2021

Reference of 53297-68-0, A common heterocyclic compound, 53297-68-0, name is 2-Chloro-4-sulfamoylaniline, molecular formula is C6H7ClN2O2S, 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 the carboxylic acid and aniline shown above, in pyridine at O0C, was added POCl3 dropwise for 5 min. The reaction was complete after stirring at O0C for an additional 50 min. The reaction mixture was quenched by addition Of H2O (1 mL), then concentrated in vacuo to light brown oil which was diluted with CH2Cl2 (200 ml). The organic layer was washed with H2O (1 x 50 ml), saturated NaHCO3 solution (1 x 50 ml), then brine (1 x 50 ml). The organic solution was dried over Na2SO4 and concentrated to dryness. The resulting oil was triturated with EtOH to give light yellow solid. To the mixture was added H2O to collect more solid. The light yellow solid was collected by vacuum filtration and dried under high vacuum for 16 hrs to yield 930 mg (72%) of product. Additional product (132 mg, 10%) was recovered by extraction of the filtrate with CH2Cl2 followed by column chromatography with acetone/CH2Cl2 (20:80).

The synthetic route of 53297-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VALEANT RESEARCH & DEVELOPMENT; WO2006/26356; (2006); A2;,
Amide – Wikipedia,
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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,
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Some common heterocyclic compound, 103361-99-5, name is 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, molecular formula is C8H6FNO2, 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. SDS of cas: 103361-99-5

c. 7-fluoro-4-isobutyl-2H-1,4-benzoxazin-3(4H)-one To 3.96 g (99 mmol) of hexanes washed 60% sodium hydride in 150 ml of N,N-dimethylformamide was added portionwise as a solid 15 g (90 mmol) of 7-fluoro-2H-1,4-benzoxazin-3(4H)-one. When the addition was complete the reaction was stirred at room temperature for 10 min, after which time 19.8 g (108 mmol) of isobutyl iodide was added. The reaction was then stirred overnight before quenching into 200 ml of water. The aqueous phase was extracted with EtOAc (2*150 ml) and the combined organics were dried over Na2 SO4, filtered and evaporated in vacuo to give the desired alkylated product, as a yellow oil (13 g, 65% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103361-99-5, its application will become more common.

Reference:
Patent; Rohm and Haas Company; US5393735; (1995); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 402-46-0, These common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, 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.

Step b N-[(1-Oxo-2-oxo-2-chloro)ethyl]-4-(fluoro)benzenesulfonamide Combine 4-(fluoro)benzenesulfonamide (1.12g, 6.4mmol) and oxalyl chloride (15mL) and reflux for 9 hours. Evaporate the excess oxalyl chloride in vacuo to give the title compound.

Statistics shows that 4-Fluorobenzenesulfonamide is playing an increasingly important role. we look forward to future research findings about 402-46-0.

Reference:
Patent; Merrell Pharmaceuticals Inc.; US5606063; (1997); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 16091-26-2,Some common heterocyclic compound, 16091-26-2, name is 3′-Aminobenzanilide, molecular formula is C13H12N2O, 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.

In a 250 mL three-necked flask equipped with a stirrer, a thermometer and a reflux condenser (with a water separator), 130.0 g of methyl chloroacetate was added.42.4 g of m-anilinoaniline was added under stirring.24.5 g of sodium carbonate was uniformly mixed under stirring, and the temperature was raised to 100 to 105 C, and refluxed for 2.0 h. 4.2 g of potassium bromide and 0.3 g of zinc powder were added, and the mixture was refluxed at 110 to 130 C for 3.0 h. The sample was sampled and detected by high pressure liquid chromatography, and the purity of the target product was 99.2%. After methyl chloroacetate was distilled off under reduced pressure, acetic acid was added to obtain an acetic acid solution of m-benzoylamino-N,N-di(methyl acetate) aniline in a yield of 98.4%.

The synthetic route of 16091-26-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central South University of Forestry and Technology; Zhao Ying; Hu Renjie; Xiong Yuanfu; Zhao Qi; Yuan Yao; Tan Xiaoyan; (8 pag.)CN109796365; (2019); A;,
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Amide – an overview | ScienceDirect Topics

Synthetic Route of 120157-97-3, A common heterocyclic compound, 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine, molecular formula is C13H18BrNO2, 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: A mixture of N-boc-2-(4-bromophenyl)ethylamine, the desiredarylboronic acid (a-m) (1.2 equiv), tetrakis(triphenylphosphine)-palladium(0) (0.04 equiv), Na2CO3 (5 equiv) in degassed toluene/H2O (5/2) was refluxed for 18 h. The reaction mixture was filteredthrough Celite and concentrated in vacuo. The resulting residuewas dissolved in in EtOAc (200 mL), washed with H2O (200 mL 2) and brine (200 mL). The organic layer was dried with anhydrousNa2SO4 and concentrated in vacuo. The residue was purified by columnchromatography on SiO2. Using Method E, 13 (1.00?g, 3.3?mmol), 3-fluorophenylboronic acid (0.56?g, 4.0?mmol), tetrakis(triphenylphosphine)palladium(0) (0.15?g, 0.1?mmol), Na2CO3 (1.77?g, 16.7?mmol) in toluene/H2O (33?ml/13.3?ml), followed by 4.0?M HCl in dioxane (2.50?ml, 10.0?mmol) gave 14d as a white solid (0.52?g, 62%); Rf?=?0.00 (EtOAc 9: acetone 1): 1H NMR (DMSO-d6, 400?MHz) delta 2.98-3.09 (m, NH3CH2CH2), 7.17-7.52 (m, 6 ArH), 7.68 (d, J?=?8.0?Hz, 2 ArH), 8.34 (s, NH3); 13C NMR (DMSO-d6, 100?MHz) delta 33.0 (NCH2CH2), 113.6 (d, JC-F?=?21.8?Hz), 114.5 (d, JC-F?=?20.9?Hz), 123.0 (d, JC-F?=?2.4?Hz), 127.4, 129.8, 131.3 (d, JC-F?=?8.5?Hz), 137.6 (d, JC-F?=?2.1?Hz), 137.9, 142.8 (d, JC-F?=?7.7?Hz), 163.2 (d, JC-F?=?241.7?Hz) (12 ArC).

The synthetic route of 120157-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yeon, Seul Ki; Choi, Ji Won; Park, Jong-Hyun; Lee, Ye Rim; Kim, Hyeon Jeong; Shin, Su Jeong; Jang, Bo Ko; Kim, Siwon; Bahn, Yong-Sun; Han, Gyoonhee; Lee, Yong Sup; Pae, Ae Nim; Park, Ki Duk; Bioorganic and Medicinal Chemistry; vol. 26; 1; (2018); p. 232 – 244;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 63920-73-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-(methylthio)phenyl)-picolinaldehyde (13.10 g, 32.46 mmol) and 2-amino-4,6-dimethoxybenzamide (6.68 g, 34.08 mmol) in N,N-dimethylacetamide (150 ml) was added NaHSO3 (8.90 g, 48.69 mmol) and p-toluenesulfonic acid monohydrate (6.17 g, 32.46 mmol). The reaction mixture was stirred at 120 C. for 14 h. After that time the reaction was cooled to rt, concentrated under reduced pressure, diluted with saturated Na2CO3 (150 mL) and the precipitated solids were collected by filtration, washed with water and dried under vacuum. The product was washed with diethyl ether and dried to give 2-(5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-(methylthio)phenyl)-pyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one (17.38 g, 92%) as light yellow solid: ESI MS m/z 580 [M+H]+.

The synthetic route of 2-Amino-4,6-dimethoxybenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; Fairfax, David John; Martin, Gregory Scott; Quinn, John Frederick; Duffy, Bryan Cordell; Wagner, Gregory Steven; Young, Peter Ronald; US2014/140956; (2014); A1;,
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 703-12-8 as follows. Safety of 4-Bromo-N-methylbenzenesulfonamide

To a solution of 4-bromo-N-methylbenzenesulfonamide (2, 1.05 g, 4.20 mmol) and triisopropyl borate (1.45 mL, 6.30 mmol) in tetrahydrofuran (8.40 mL) was added n-Butyl Lithium (4.20 mL, 10.5 mmol) at -70 C. The mixture was slowly warmed to 0 C, then 10% HCl solution was added until pH 3-4. The resulting mixture was extracted with EtOAc. The organic layer was extracted with NaOH (2M) and the aqueous phase washed with diethyl ether. The aqueous phase was acidified to pH 3, extracted with EtOAc (impurities and unconsumed reactant were still present) was dried over Na2SO4, and evaporated under reduced pressure. The residue was triturated with diethyl ether to give [4- (methylsulfamoyl)phenyl]boronic acid (187 mg, 0,8700 mmol, 21% yield). (0781) Analytical data: (0782) 1H NMR (200 MHz, DMSO) delta 7.96 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.0 Hz, 2H), 7.42 (q, J = 4.9 Hz, 1H), 2.39 (d, J = 5.0 Hz, 3H); (0783) 13C NMR (50 MHz, DMSO) delta 140.6, 134.8, 125.7, 28.8.

According to the analysis of related databases, 703-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HEPAREGENIX GMBH; PRAEFKE, Bent; KLOeVEKORN, Philip; SELIG, Roland; ALBRECHT, Wolfgang; LAUFER, Stefan; (157 pag.)WO2019/149738; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H10ClNO2

2) 2-chloro-N-(3-methoxyphenyl)acetamide (3.1g, 16 mmol) and anhydrous AlCl3 powder (4.4g,32 mmol) is heated and stirred at 120C for 10 minutes and exhibit a melting state. The temperature is elevated gradually to 240C in 40 minutes and then stirred 5 minutes. The reaction is allowed to cool to obtain a brown powder. The solid powder is poured into a mixture of 100g of crushed ice and 50ml of concentrated hydrochloric acid. The mixture is stirred for 10 minutes and then reflux for 10 minutes, and allowed to cool to precipitate a light yellow powder, which is filtered out and recrystallized in water to obtain 1.5g of 6-hydroxy-indoline-2-one, with a yield of 62%.

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:
Patent; Jiangsu Guohua Investment Co., Ltd; Shanghai Institute of Pharmaceutical Industry; EP2322520; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 142-26-7, A common heterocyclic compound, 142-26-7, name is N-Acetylethanolamine, molecular formula is C4H9NO2, 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.

The title product of Preparation 29 (600 mg, 2.16 mmol), N-(2-hydroxyethyl)acetamide (276 mg, 2.68 mmo), triphenylphosphine (710 mg, 2.71 mmol) were mixed under Ar atmosphere followed by the addition of dry THF (5 ml). The mixture was cooled at 0 and DIAD was added drop wise. The reaction mixture was allowed to warm to rt and then stirred overnight. Solvent was removed and the residue thus obtained was partitioned between water and ethyl acetate. The organic layer was washed with water and brine. It was dried and solvent removed to yield a crude product that was purified according to purification method A to yield the title compound as a solid. 130 mg (17% yield) of the title product were obtained as a solid.LRMS: m/z 363 (M+1fRetention time: 4.32 min (method B)H NMR (200 MHz, DMSO-D6) delta ppm 0.92 (t, 3 H) 1.29 – 1.45 (m, 2 H) 1.55 (d,J=7.14 Hz, 2 H) 1.77 (s, 3 H) 2.20 (s, 6 H) 3.06 (t, J=6.59 Hz, 2 H) 3.24 – 3.45(m, 2 H) 3.85 – 4.01 (m, 2 H) 7.23 (s, 2 H) 7.96 – 8.07 (m, 1 H) 8.85 – 8.93 (m, 1H)

The synthetic route of 142-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; GRIMA POVEDA, Pedro Manuel; AGUILAR IZQUIERDO, Nuria; MIR CEPEDA, Marta; CARRASCAL RIERA, Marta; TERRICABRAS BELART, Emma; GRACIA FERRER, Jordi; CASALS COLL, Gaspar; WO2011/35900; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics