Amides-buliding-blocks

Some common heterocyclic compound, 64214-66-0, name is 4-Chloro-N-methoxy-N-methylbutanamide, molecular formula is C6H12ClNO2, 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. 64214-66-0

Step B 3-chloropropyl 3,5-dimethylphenyl ketone A solution of 10.2 mL (13.9 g; 72 mmol) 5-bromo-m-xylene in 200 mL of anhydrous tetrahydrofuran was stirred under nitrogen at -78 C. as 35.8 mL (84 mmol) of 2.5M n-butyllithium in tetrahydrofuran was added dropwise. After 15 minutes at -78 C., a solution of 10.0 g (60 mmol) of 4-chloro-N-methoxy-N-methylbutyramide (from Step A) in 30 mL of anhydrous tetrahydrofuran was added dropwise over 25-30 minutes. The resulting solution was maintained at -78 C. for 45 minutes and then warmed briefly to room temperature. The reaction was quenched by addition of 40 ml of 2N hydrochloric acid and then partitioned between ethyl acetate and water. The organic phase was washed with saturated aqueous sodium bicarbonate solution and then saturated aqueous sodium chloride solution. The organic solution was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography of the residue afforded 8.91 g (70%) of an oil, which had satisfactory purity by 1 H NMR (CDCl3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64214-66-0, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US5756507; (1998); A;,
Amide – Wikipedia,
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72791-76-5, The chemical industry reduces the impact on the environment during synthesis 72791-76-5, name is Benzyl bis(2-chloroethyl)carbamate, I believe this compound will play a more active role in future production and life.

2-phenylacetonitrile (5.000 g, 42.680 mmol) and sodium hydride (60.00%, 3.755 g, 93.897 mmol) was dissolved in N,N-dimethylformamide (100 mL) at 0 C and stirred for 30 minutes then benzyl bis(2-chloroethyl)carbamate (11.787 g, 42.680 mmol) was added thereto after further stirring at 60 C for 3 hours, the reaction was terminated by lowering the temperature to room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by column chromatography (SiO2, 40 g cartridge; ethyl acetate / hexane = 30% to 100%) and concentrated to give the title compound (7.500 g, 54.8%) as a white solid.

The chemical industry reduces the impact on the environment during synthesis Benzyl bis(2-chloroethyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

869494-16-6, 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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, A new synthetic method of this compound is introduced below.

A suspension of 3,6-diaza-bicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (182 mg, 0.918 mmol), 2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (819 mg, 3.67 mmol) and K2C03(S) (634 mg, 4.59 mmol) in DMSO (918 was heated to 90 ¡ãC, then treated with water (5 mL). The resulting mixture was stirred for 1 hour at 90 ¡ãC, then cooled to ambient temperature and filtered to cleanly provide the title compound (1.0 g, 41percent yield). MS (apci) m/z = 320.1 (M+H).

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:
Patent; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 72179-84-1 name is (Methylsulfamoyl)amine, 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. 72179-84-1

Example 67 (100 mg, 0.259 mmol) was dissolved in tetrahydrofuran (4 mL) and carbonyldiimidazole (63.1 mg, 0.389 mmol) was added. The mixture was heated to 60 C for 1 hour. More carbonyldiimidazole (63.1 mg, 0.3 89 mmol) was added, and the resultant solution was stirred at 60 C for 1 hour. The solution was cooled down to room temperature and was then added dropwise through a syringe to a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.117 mL 0.778 mmol, DBU) and N-methylsulfuric diamide (86 mg, 0.778 mmol) in 0.6 mL tetrahydrofuran. The resulting mixture was stirred at room temperature overnight. The mixture was acidified with 1 N HC1 to pH=6-7 and then extracted with ethyl acetate 3 times. The organic layers were combined and concentrated. The residue was diluted with methanol to give a solution which was purified by preparative HPLC (0.1% CF3CO2H in H20/CH3CN) and lyophilized to give the titled compound (72.5 mg, 0.152 mmol, 58.5% yield). ?H NMR (400 MHz, DMSO-d6) ppm 11.39 (s, 1H), 7.46 (q, J = 4.9, 4.5 Hz, 1H), 7.14 (dd, J = 56.8, 38.2 Hz, 5H), 6.50 (s, 2H), 3.74 (s, 6H), 3.67-3.58 (m, 1H), 3.46 (d, J = 19.0 Hz, 4H), 3.19 (s,1H), 2.60 (s, 3H), 2.40 (s, 2H), 1.98 (s, 3H), 1.82 (a, J = 16.8 Hz, 2H); LC-MS (ESI+) m/z 478.2 (M+H), RT = 1.9 19 minutes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Methylsulfamoyl)amine, and friends who are interested can also refer to it.

Reference:
Patent; ABBVIE INC.; BLACK, Lawrence, A.; BUNNELLE, William, H.; CHEN, Da; CLAPHAM, Bruce; DEGOEY, David, A.; DENG, Xiangjun; FU, Liqiang; HAZELWOOD, Lisa, A.; KONG, Linglong; LANG, Qingyu; LEE, Chih-Hung; LI, Mingfeng; LUNDGAARD, Greta, L.; PATEL, Meena, V.; TAO, Ruihong; ZHANG, Lin; ZHANG, Qingwei; ZHENG, Qiangang; ZHU, Wei; (289 pag.)WO2017/177004; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

22958-64-1, 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. 22958-64-1, name is 2-(4-Sulfamoylphenyl)acetic acid belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00382] 1H NMR (400 MHz, DMSO-cfe) d 7.80 – 7.74 (m, 2H), 7.48 (d, J= 8.4 Hz, 2H), 7.41 – 7.29 (m, 3H), 7.22 – 7.15 (m, 2H), 7.07 (td, J= 8.3, 1.8 Hz, 1H), 3.95 (s, 2H), 3.75 (s, 2H), 2.81 – 2.64 (m, 8H); LC-MS Rt 0.53 min, MS m/z [M+H]+ 499.4

The synthetic route of 2-(4-Sulfamoylphenyl)acetic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; KOUNDE, Cyrille; SIM, Wei Lin Sandra; SIMON, Oliver; WANG, Gang; YEO, Hui Quan; YEUNG, Bryan KS; YOKOKAWA, Fumiaki; ZOU, Bin; (122 pag.)WO2019/244047; (2019); 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 1015-89-0 as follows. 1015-89-0

(ii) BDS, THF, reflux, 24 h; (yield 20percent)

According to the analysis of related databases, 1015-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ROBERTS, Edward; MITTAPALLI, Gopi Kumar; VELLUCCI, Danielle; YANG, Jun; GUERRERO, Miguel; URBANO, Mariangela; ROSEN, Hugh; WO2014/116684; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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