Category: amides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6292-59-7, 6292-59-7

To a solution of 4-tert-butyl benzene sulfonamide compound of formula-6 (48 g) in toluene (600 ml), potassium carbonate (35 g) and tetra butyl ammonium bromide (10 g) was added and the reaction mixture was heated to 50¡ãC. A solution of 5-(2- methoxyphenoxy)-2-(2’pyrimidinyl)-4,6-dichloro pyrimidine compound of formula- 5 (60 g) in toluene (1200 ml) was added slowly to the reaction mixture and it was refluxed using dean stark apparatus for 10 hrs. The reaction mixture was cooled to 25¡ãC and acidified with aqueous hydrochloric acid. The reaction mixture was stirred for an hour. The solid obtained was filtered, washed with water and dried to get the title compound. Yield: 87 g

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(tert-Butyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MSN LABORATORIES LIMITED; WO2009/95933; (2009); A2;,
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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, A new synthetic method of this compound is introduced below., 67442-07-3

Benzylmagnesium chloride (1.0 M in diethyl ether, 50.0 mL) was treated with 2-chloro-N-methoxy-N-methylacetamide (5.16 g, 37.5 mmol) in tetrahydrofuran (200 mL) at -78¡ã C. drop wise. The reaction was allowed to warm slowly to room temperature overnight and quenched with 1N hydrochloric acid. The layers were separated and the organic phase dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel; elution with hexanes) to provide the title. 1H NMR (300 MHz, DMSO-d6) delta 3.87 (s, 2H), 4.62 (s, 2H), 7.25 (m, 5H); MS (DCI/NH3) m/z 186 (M+NH4)+.

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; Kolasa, Teodzyj; Patel, Meena; Mortell, Kathleen H.; Matulenko, Mark A.; Hakeem, Ahmed A.; Bhatia, Pramila A.; Wang, Xueqing; Daanen, Jerome F.; Latshaw, Steven P.; Stewart, Andrew O.; US2005/176727; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common compound: 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 6292-59-7

General procedure: The N-R-sulfonyldithiocarbimate potassium salts were prepared in dimethylformamide (DMF) from the sulfonamides in reaction with carbon disulfide and potassium hydroxide analogously as described in the literature [9,22,23]. Carbon disulfide (10mmol) and potassium hydroxide (20mmol) were added to a solution of the corresponding sulfonamide (10mmol) in DMF (25mL). The mixture was stirred for approximately 4h up to the total consumption of KOH. Upon the addition of 20mL of ice cold ethanol, a yellowish solid is formed. The product was separated by filtration, washed with ice ethanol, ethyl acetate, diethyl ether, and dried under reduced pressure (yields 70-85%, based on the sulfonamide). The compounds 1a-e are described in literature [9,22,23]. The data for the new potassium dithiocarbimates 1f-h are as follows.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6292-59-7, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Vidigal, Antonio E.C.; Rubinger, Mayura M.M.; de Queiroz, Luan F.; da Silva, Lucas F.; Zambolim, Laercio; Guilardi, Silvana; Souza, Rafael A.C.; Ellena, Javier; Wetler, Emiliana B.; Oliveira, Marcelo R.L.; Inorganica Chimica Acta; vol. 486; (2019); p. 724 – 732;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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. 67442-07-3

To an oven dried, N2-flushed 100 mL round bottom flask was added 5-cyclohexyl-5-methylimidazolidine-2,4-dione (Example 2.47d) (6.77 g, 32.9 mmol), K2CO3 (6.80 g, 49.3 mmol) 32 mL of anhydrous DMF and commercially available 2-chloro-N-methoxy-N-methylacetamide (4.74 g, 34.5 mmol). The reaction was stirred at 50¡ã C. for 12 h. The reaction was cooled and 70 mL water was added with stirring. The precipitate was filtered and dried to afford 8.9 g (92percent) of 2-(4-cyclohexyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-N-methoxy-N-methylacetamide as a white solid. (0741) To an oven dried, N2-flushed 100 mL round bottom flask was added 2-(4-cyclohexyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-N-methoxy-N-methylacetamide (8.90 g, 29.9 mmol), Cs2CO3 (13.65 g, 41.9 mmol), 30 mL DMF and methyl iodide (2 mL, 31.4 mmol). The reaction was stirred for 24 hours and 60 mL water was added. The mixture was extracted with ether (3¡Á50 mL). The combined organic layers were washed with water (1¡Á100 mL), brine and dried with Na2SO4. The solvent was evaporated, and the residue was purified by column chromatography utilizing a Silicycle column (120 g) and elution with 20-70percent ethyl acetate/hexane to afford 8.2 g (88percent) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) delta 4.28 (s, 2H), 3.73 (s, 3H), 3.10 (s, 3H), 2.78 (s 3H), 1.79-1.49 (m, 6H), 1.39-1.25 (m, 4H), 1.23-0.82 (m, 4H); MS 312 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 67442-07-3, its application will become more common.

Reference:
Patent; SENOMYX, INC.; Chumakova, Lyudmyla; Patron, Andrew; Priest, Chad; Karanewsky, Donald; Kimmich, Rachel; Boren, Brant Clayton; Hammaker, Jeffrey Robert; Chumakov, Volodymyr; Zhao, Wen; Noncovich, Alain; Ung, Jane; (146 pag.)US2015/376136; (2015); 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. 630-22-8, name is 2,2-Dimethylpropanethioamide, A new synthetic method of this compound is introduced below., 630-22-8

To a solution of N-(3-(2-bromo-2-(2-(methylthio)pyrimidin-4-yl)acetyl)-2- chloro-5-fluorophenyl)-pivalamide (AT, 489 mg, 1.03 mmol) in DMA (4.7 mL) under Ar at rt was added 2,2-dimethylpropanethioamide (131 mg, 1.12 mmol). The reaction mixture was stirred at rt for 1 h, and then heated to and maintained at 80 C for 3 h. The reaction was judged complete by LCMS. The reaction mixture was diluted with water and twice extracted with EtOAc. The organic phases were combined, washed with brine, dried (Na2S04), and concentrated. The resulting residue was adsorbed onto silica gel and purified by flash chromatography on silica gel using an EtOAc :heptanes (0-15%) elution gradient to furnish N-(3 -(2 -tert-butyl-5 -(2-(methylthio)pyrimidin-4-yl)thiazol-4-yl)-2-chloro-5 – fluorophenyl)pivalamide (175 mg, 0.36 mmol, 38 %) as a white foam: LCMS (m/z): 493.1 (MH+), tR = 1.42 min.

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; NOVARTIS AG; MADERA, Ann Marie; POON, Daniel; SMITH, Aaron; WO2011/161216; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

632-24-6, 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. 632-24-6, name is 2-(Sulfamoylamino)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 2-Sulfamoylbenzoic acid or 3-sulfamoylbenzoic acid(0.25 mmol) was placed in a 25-mL round-bottomed flaskand SOCl2 (3 mL) was added dropwise at 0C with stirring.The reaction mixture was placed in an 80C oil bath andrefluxed for 2 h. The reaction mixture was cooled to roomtemperature and the volatiles were removed in vacuum byrotary evaporation, leaving a light-yellow oil. Separately, thesolution of the benzyl-protected L-proline 4a (60 mg, 0.25mmol) and TEA (56 mg, 0.55 mmol) in anhydrous DCM (5mL) was prepared under argon. The solution of the obtainedbenzoyl chloride in anhydrous DCM (5 mL) was added tothe solution of the L-proline at 0 C and the reaction mixturewas stirred at room temperature until completion. The mixturewas diluted with DCM (70 mL) and washed successivelywith sat. NaHCO3 (60 mL) and brine (60 mL). Theorganic layer was dried over Na2SO4, filtered and concentratedunder reduced pressure. The residue was purified byflash column chromatography (PE: EA=2: 1) to afford 6b or7b.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Liu, Xinyu; Dong, Shengjie; Ma, Yuru; Xu, Hu; Zhao, Hongxia; Gao, Qingzhi; Medicinal Chemistry; vol. 15; 2; (2019); p. 196 – 206;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

2895-21-8, 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 2895-21-8 as follows.

EXAMPLE 1 The compound N-isopropyl-alpha-chloroacetamide (2.71 g; 0.02 mole) and benzyltriethylammonium chloride (0.09 g) were dissolved in methylene chloride (50 ml) in a 100 ml flask. A 50% by weight sodium hydroxide solution (16 g) was added to the mixture, and the mixture was stirred vigorously at 40 C. for three days. Thereafter, the organic phase was separated, dried and evaporated. The residue of the evaporation (found to be four parts product per part starting material) was recrystallized from ethyl alcohol to yield 0.7 g (36%) of 1,4-diisopropyl-2,5-diketopiperazine. All spectral data were consistent with this structure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2895-21-8, and friends who are interested can also refer to it.

Reference:
Patent; Monsanto Company; US4694082; (1987); A;,
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 90-16-4 as follows. 90-16-4

General procedure: Propargyl bromide (1.2 mmol) was added to a solution of 1aa or 1bb or 1cc (1.0 mmol) and K2CO3 (3.0 mmol) in CH3CN (25 mL) under a nitrogen atmosphere. The mixture was stirred at room temperature for 3 h. After completion of the reaction (confirmed by TLC), the mixture was diluted with ice-water (60 mL) and extracted with EtOAc(3¡Á15 mL). The organic layers were collected, combined, dried over anhydrous Na2SO4, filtered and concentrated under low vacuum. The residue was purified by column chromatography using hexane- EtOAc as eluent to afford the title compound.

According to the analysis of related databases, 90-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Reddy, Gangireddy Sujeevan; Snehalatha, Ampalam Venkata; Edwin, Rebecca Kristina; Hossain, Kazi Amirul; Giliyaru, Varadaraj Bhat; Hariharapura, Raghu Chandrashekhar; Gautham Shenoy; Misra, Parimal; Pal, Manojit; Bioorganic Chemistry; vol. 91; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

354-38-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 354-38-1 name is 2,2,2-Trifluoroacetamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Trifluoroacetamide (4.4 g, 38.9 mmol), magnesium oxide (3.1 g, 77.7 mmol), rhodium(II) acetate dimer (217 mg, 0.49 mmol) and iodobenzene diacetate (9.4 g, 29.1 mmol) were added to a solution of 3-(2,6-difluoro-phenylmethanesulfanyl)-5,5-dimethyl- 4,5-dihydroisoxazole (5 g, 19.4 mmol) in dichloromethane (150 ml) under nitrogen and the grey suspension was stirred for 12 hours at room temperature. The mixture was filtered and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (eluent: hexane / ethyl acetate) to give the product (Compound No.1.09 of Table 65) (6.7 g, 90% purity, 84% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2,2-Trifluoroacetamide, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA LIMITED; WO2006/37945; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, 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. 830-43-3

In a 20-mL screw-cap vial, 250 mg (0.75 mmol) 2-(2-chlorophenyl)-1-(4-chlorophenyl)- IH-imidazole-4-carboxylic acid, 18.3 mg DMAP (0.15 mmol), 1.25 g PS-Carbodiimide (1.5 mmol) (polystyrene-supported cyclohexylcarbodiimide , Argonaut Technologies Inc. , San Carlos, CA), 169 mg a,a,a-trifluoro-p-toluenesulfonamide (0.75 mmol), and 12 mL dichloromethane were added, and the reaction mixture was mixed by orbital shaking at rt overnight. The reaction mixture was filtered through a filter tube (polypropylene frit), and the filtrate was evaporated under reduced pressure. The crude product was redissolved in 2 mL MeOH and purified by preparative HPLC to give 39.3 mg of N-{ [2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4- yl]carbonyl}-4-(trifluoromethyl)benzenesulfonamide (beige solid, 10% yield). ?H NMR (400 MHz, CD3COCD3) 8 8.25 (d, 2 H), 7.85 (s, 1 H), 7.75 (s, 2H), 7.20-7.40 (m, 6 H), 6.95 (t, 2 H); LC-MS m/z 540 (MH+), retention time 3.36 min (method 2).

Statistics shows that 830-43-3 is playing an increasingly important role. we look forward to future research findings about 4-(Trifluoromethyl)benzenesulfonamide.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2005/99705; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics