Month: December 2020

1885-32-1, The chemical industry reduces the impact on the environment during synthesis 1885-32-1, name is 2-Amino-3-methylbenzamide, I believe this compound will play a more active role in future production and life.

Preparation 14 2-(5-Acetyl-2-ethoxybenzamido)-3-methylbenzamide Oxalyl chloride (3.66 g, 0.0288 mol) was added dropwise to a stirred solution of 5-acetyl-2-ethoxy-benzoic acid (3 g, 0.00144 mol) and dimethylformamide (0.1 ml) in dichloromethane (15 ml). The mixture was stirred at room temperature for 3 hours, then the solvent evaporated under vacuum and the residue azeotroped with hexane (3*50 ml). The crude acyl chloride was dissolved in dichloromethane (20 ml) and the solution added dropwise to a stirred solution of 2-amino-3-methylbenzamide (2.16 g, 0.0144 mol) in pyridine (40 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for a further 18 hours. The solvent was removed by evaporation under vacuum, the residue dissolved in dichloromethane (50 ml) and this solution then washed with saturated aqueous sodium carbonate solution (50 ml), 2N hydrochloric acid (50 ml) and brine (50 ml), then dried (Na2SO4) and evaporated under vacuum. Trituration of the residue with diethyl ether gave the title compound as a white solid (2.14 g, 44%), m.p. 214-216 C.

The chemical industry reduces the impact on the environment during synthesis 2-Amino-3-methylbenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Cell Pathways, Inc.; US6562830; (2003); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

127828-22-2, 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. 127828-22-2 name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, 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.

A stirred solution of 4-chloro-3-nitroquinoline (31.4 g, 0.151 mol) in 500 mL of anhydrous CH2Cl2, under N2, was treated with triethylamine (43 mL, 0.308 mol) and tert-butyl 2-(2-aminoethoxy)ethylcarbamate (0.151 mol). After stirring overnight, the reaction mixture was washed with H2O (2¡Á300 mL) and brine (300 mL). The organic portion was dried over Na2SO4 and concentrated to give a bright yellow solid. Recrystallization from ethyl acetate/hexanes gave 43.6 g of tert-butyl 2-{2-[(3-nitroquinolin-4-yl)amino]ethoxy}ethylcarbamate as bright yellow crystals.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; 3M Innovative Properties Company; US6660735; (2003); B2;; ; Patent; 3M Innovative Properties Company; US6664265; (2003); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

177906-48-8, 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. 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, A new synthetic method of this compound is introduced below.

1.8 g of LiAlH4 was added to a solution of 2.1 g of intermediate 41 in 50 mL of THF, and heated to reflux for 2 hours. After the reaction was completed, 50 mL of saturated ammonium chloride solution was carefully added under an ice bath to quench the reaction. Separate the organic phase, extract the aqueous phase three times with dichloromethane and incorporate the organic phase, It was washed successively with saturated aqueous ammonium chloride solution and saturated brine, and then dried over anhydrous sodium sulfate, The sodium sulfate was removed by filtration and concentrated to obtain the crude product. The crude product was isolated by column chromatography (200-300 mesh silica gel, eluent dichloromethane: methanol = 3: 1) to obtain pure intermediate 42.

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; ShanghaiTech University; Tao Houchao; Zhao Fei; (85 pag.)CN110894209; (2020); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

147962-41-2, name is N-Propylsulfamide, 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. 147962-41-2

General procedure: Under nitrogen atmosphere, a mixture of sulfonamide 2a-h (1 mmol), maleic anhydride derivatives (2 mmol), and H6P2W18O62 catalyst (2 mmol%) in acetonitrile (2 mL), was stirred at reflux. Reaction was monitored by TLC. After achieving the reaction, dichloromethane (2 ¡Á10 mL) was added and the catalyst was filtered; water (10 mL) was then added. The organic layers were combined and dried over anhydrous sodium sulfate and removed under reduced pressure. The residue obtained was purified by flash chromatography (Merck silica gel 60H, CH2Cl2/MeOH, 9:1) to afford the corresponding sulfonyl maleimide derivatives.

Statistics shows that 147962-41-2 is playing an increasingly important role. we look forward to future research findings about N-Propylsulfamide.

Reference:
Article; Bougheloum, Chafika; Guezane Lakoud, Samia; Belghiche, Robila; Messalhi, Abdelrani; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 10; (2016); p. 1344 – 1350;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

609-66-5, 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. 609-66-5 name is 2-Chlorobenzamide, 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.

General procedure: To a 25 mL Schlenk tube containing a solution of 2 in 2 mL of THF was added amide (1.0 mmol) and (EtO)3SiH (0.50 g, 3.0 mmol). The reaction mixture was stirred at 60 C until there was no amide left (monitored by TLC and GC-MS). The product was purified according to literature procedures by Beller

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; Ren, Shishuai; Wang, Yangyang; Yang, Fei; Sun, Hongjian; Li, Xiaoyan; Catalysis Communications; vol. 120; (2019); p. 72 – 75;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 354-38-1, name is 2,2,2-Trifluoroacetamide, molecular formula is C2H2F3NO, 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. 354-38-1

(rac)-2,2,2-Trifluoro-N-[methyl(3-nitrobenzyl)oxido-lambda6-sulfanylidene]acetamide To a suspension of (rac)-1-[(methylsulfinyl)methyl]-3-nitrobenzene (16.6 g; 83.1 mmol), trifluoroacetamide (18.8 g; 166.1 mmol), magnesium oxide (13.4 g; 332.3 mmol) and rhodium(II)-acetat dimer (1.7 g; 8.3 mmol) in DCM (2290 mL) was added iodobenzene diacetate (40.1 g; 124.6 mmol) at room temperature. The batch was stirred for 16 hours at room temperature, filtered and concentrated. The residue was purified by chromatography (DCM / ethanol 97:3) to give the desired product (25.6 g; 82.4 mmol). 1H NMR (400MHz, CDCl3, 300K) delta = 8.36 (m, 1H), 8.31 (m, 1H), 7.80 (m, 1H), 7.69 (m, 1H), 4.91 (d, 1H), 4.79 (d, 1H), 3.28 (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 354-38-1, its application will become more common.

Reference:
Patent; Bayer Intellectual Property GmbH; EP2527332; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

45267-19-4, Adding a certain compound to certain chemical reactions, such as: 45267-19-4, name is N-(3-(Dimethylamino)propyl)tetradecanamide, 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 45267-19-4.

2) Quaternization reaction: 92.3131.26g was added to a three-necked flask equipped with a reflux condenser.Myristyl propyl dimethyl tertiary amine and 13.40 g of sodium chloroacetate(The molar ratio of myristamide propyl dimethyl tertiary amine to sodium chloroacetate is 1: 1.15), add 30.50g of water to dissolve sodium chloroacetate exactly,Add 15.25g of isopropanol and adjust the pH between 7 and 8.The quaternization reaction was carried out by heating to 80 C, and the free amine value was measured every hour. After 6 hours, the conversion rate was no longer increased, and the reaction was stopped to obtain a crude product.Rotary evaporation to remove isopropanol and water from the crude product.Then add 3 volumes of isopropyl alcohol to dissolve and filter to remove unreacted sodium chloroacetate.Final rotary evaporation to recover isopropanol,Getting myristyl propyl lysine,That is, the betaine type amphoteric surfactant of the present invention has a yield of 94.86%.

According to the analysis of related databases, 45267-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou University; Shang Xiaoqin; Wang Xinrui; Liu Peng; Liu Rufeng; Jiang Huihua; Chen Haoliang; (13 pag.)CN106800520; (2018); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

4093-29-2, 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. 4093-29-2, name is Methyl 4-acetamido-2-methoxybenzoate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To methyl 4-acetamido-2-methoxybenzoate (299 mg, 1.34 mmol) in acetic anhydride (3 ml) stirred under nitrogen at -10 C was added concentrated nitric acid (0.35 ml) dropwise. After then stirring at 0 C for 10 min the reaction mixture was partitioned between ethyl acetate (20 ml) and water (20 ml). The aqueous layer was further extracted with ethyl acetate (2 x 10 ml) and the combined organic extract washed with saturated sodium bicarbonate solution (2 x 10 ml), brine (2 x 10 ml), dried (MgSO_ and evaporated to give methyl 4-acetamido-2-methoxy-5 -nitrobenzoate (301 mg, 84%) as a dull orange powder. nmr (400 MHz, CDC13) delta 2.33, s, 3H, AcNH; 3.91, s, 3H, 2-MeO or COOMe; 4.03, s, 3H, COOMe or 2-MeO; 8.63, s, IH, H3 or H6; 8.84, s, IH, H6 or H3; 10.89, br, NH.

The synthetic route of Methyl 4-acetamido-2-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; MARTIN, Roger, Francis; WHITE, Jonathan; LOBACHEVSKY, Pavel; WINKLER, David; SKENE, Colin; MARCUCCIO, Sebastian; WO2011/123890; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6292-59-7, 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 6292-59-7 as follows.

p-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)[2,2′-bipyrimidin]-4-yl] benzene sulfonamide potassium salt compound of formula-7b: 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 500C. 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 25C.The solid obtained slurried in water and then filtered, washed with water and then dried to get the title compound. Yield: 90 gTo a solution of 4-tert-butyl benzene sulfonamide compound of formula-6 (61.3 grams) in toluene (1500 ml), potassium carbonate (77.93 grams) and tetra butyl ammonium bromide (2.77 grams) was added and the reaction mixture was heated to 50C. A solution of 5-(2-methoxyphenoxy)-2-(2’pyrimidmyl)-4,6-dichloro pyrimidine compound of formula-5a (100 grams) in toluene (1500 ml) was added slowly to the reaction mixture and it was refluxed for 10 hrs. The reaction mixture was cooled to 25C.The solid obtained was filtered and made slurry in water. The solid was filtered, washed with water followed by acetonitrile and dried. Yield: 116 grams, HPLC purity: 99.3%, MR: 202-205C.

According to the analysis of related databases, 4-(tert-Butyl)benzenesulfonamide, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MSN LABORATORIES LIMITED; WO2009/95933; (2009); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 27366-72-9, name is 2-(Dimethylamino)ethanethioamide hydrochloride, 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 27366-72-9. 27366-72-9

EXAMPLE 1 Preparation of Ethyl 2-Dimethylaminomethyl-4-thiazolecarboxylate A reaction mixture was prepared containing 15.5 g. of dimethylaminothioacetamide hydrochloride, 20.5 g. of ethyl bromopyruvate and 100 ml. of ethanol. The reaction mixture was heated to refluxing temperature for about four hours after which time the solvent was removed in vacuo in a rotary evaporator. The residue, containing ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate hydrochloride formed in the above reaction, was dissolved in a mixture of ether and water. The aqueous layer was separated. The ether layer was extracted with an equal volume of water and then discarded. The two aqueous layers were combined and washed with ether. The ether layer was again discarded and the aqueous layer cooled to a temperature in the range of 0-5 C. Solid potassium carbonate was added until the aqueous layer gave a basic reaction to litmus. An oil separated comprising ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate free base. The oily layer was extracted with ether and the ether extract separated and dried. The ether was removed by evaporation in vacuo. The resulting residue was purified by gradient high pressure liquid chromatography (silica, ethyl acetate). Ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate thus obtained had the following physical characteristics: Analysis Calculated: C, 50.45; H, 6.59; N, 13.07; S, 14.96 Found: C, 50.13; H, 6.39; N, 12.89; S, 15.04. The nmr spectrum in CDCl3 (TMS internal standard) gave the following signals (delta): 1.43 (triplet, 3H), 2.40 (singlet, 6H), 3.87 (singlet, 2H), 4.47 (quartet, 2H), 8.20 (singlet, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2-(Dimethylamino)ethanethioamide hydrochloride.

Reference:
Patent; Eli Lilly and Company; US4474794; (1984); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics