Amides-buliding-blocks

Some common heterocyclic compound, 609-66-5, name is 2-Chlorobenzamide, molecular formula is C7H6ClNO, 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. 609-66-5

General procedure: (Diacetoxyiodo) benzene (5 mmol, 1.61g) and NaHSO4.H2O (1mmol, 0.138g) were stirred for 10-15 min, at room temperature in aqueous solution of acetonitrile (5 ml water and 5 mlacetonitrile). In this reaction mixture benzamide (1mmol) was added and stirring was continuing till reaction goes to completion (TLC). After completion of reaction, the reaction mixture was quenched with water and further extracted with chloroform (3¡Á10 ml). The combined chloroform layers were washed with water (3¡Á20ml) dried over Na2SO4, and concentrated on rota-evaporator to get the crude residue. The residue was further purified by column chromatography on silica gel using ethyl acetate: hexane (1:9) as an eluent to afford pure benzoquinone.

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

Reference:
Article; Sasane, Kulbhushan A.; Telvekar, Vikas N.; Synthetic Communications; vol. 44; 4; (2014); p. 468 – 473;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

102-93-2, 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. 102-93-2 name is 3-Phenylpropanamide, 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.

DCM (20 mL) was added to a flask containing Lawesson?s reagent (2.022 g, 5.00 mmol). 3-Phenylpropanamide (1 .492 g, 10.00 mmol) was dissolved in DCM (20 mL), added tothe suspension, and stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure and purified by column chromatography (DCM) to afford the title compound (1 .07 g 1H NMR (500 MHz, ODd3) O 7.30 (t, 2H), 7.24 – 7.21 (m, 3H), 3.12 (t, 2H), 2.95 (t, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Phenylpropanamide, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLUM, Francesca; CARR, James Lindsay; SHAH, Pritom; DEL MAR JIMENEZ QUESADA, Maria; FARRE GUTIERREZ, Irene; (213 pag.)WO2016/124938; (2016); A1;,
Amide – Wikipedia,
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2675-89-0, A common compound: 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, 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.

EXAMPLE 18; N,N-Dimethylaminocarbonylmethyl 3-Aminosulfonyl-5-butylamino-4- phenoxybenzoate (Bumetanide N,N-Dimethylglycolamido Ester); [0481] Bumetanide (1.2g, 3.29 mmol) was dissolved in dimethylformamide (DMF, 10 mL) and 2- chloro-N,N-dimethylacetamide (410 muL, 3.9 mmol) was added followed by triethylamine (0.70 mL) and sodium iodide (545 mg, 3.6 mmol). The reaction was heated to 50C for 10 hours, TLC and LC/MS indicated the reaction was complete. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate, water, and brine and dried over anhydrous magnesium sulfate. The ethyl acetate was removed under reduced pressure and the product was purified via flash chromatography on silica gel to yield 685 mg (60%) of pure N,N- dimethylaminocarbonylmethyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate.

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, 2-Chloro-N,N-dimethylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROTHERAPEUTICS PHARMA, INC.; WANAKSI, Stephen; PARTRIDGE, John, J.; COLLINS, Stephen; WO2010/85352; (2010); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

108468-00-4,Some common heterocyclic compound, 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, molecular formula is C13H20N2O2, 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 solution of 4-(Boc-aminomethyl)benzylamine (1) (1.0 mmol)and TEA (3.0 mmol) in anhydrous DCM (8 mL) was cooled with anice bath, then the corresponding sulfochloride (1.1 mmol, dissolvedin 2mL anhydrous DCM) was added dropwise. The reactionmixture was allowed to stir at 0 C for 1 h. After removing thecooling bath, the resulting mixture was stirred for 5 h at roomtemperature, then diluted with saturated aqueous NaHCO3 andextracted with DCM (10 mL) for three times. The combined organiclayer was sequentially washed with water and brine, dried withanhydrous Na2SO4, and concentrated in vacuo. The crude was purifiedby column chromatography with DCM/methanol (150:1, v/v)to yield the product as a white solid [5].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108468-00-4, its application will become more common.

Reference:
Article; Bai, Renren; Sun, Jian; Liang, Zhongxing; Yoon, Younghyoun; Salgado, Eric; Feng, Amber; Oum, Yoonhyeun; Xie, Yuanyuan; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 195 – 205;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide, molecular formula is C9H12N2O, 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. 6331-71-1.

A solution of 26.4 g of 4-amino-N,N-dimethylbenzamide in 500 ml toluene and 60 g acetonylacetone is refluxed for 16 hours under a Dean-Stark water separator. The solution is washed with water and brine, dried over MgSO4, filtered and the solvent evaporated at 60 and reduced pressure. The residue is crystallized from ether-hexane 1:1 to yield 1-(4-dimethylcarbamoylphenyl)-2,5-dimethyl-1H-pyrrole, m.p. 102-104.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-N,N-dimethylbenzamide, its application will become more common.

Reference:
Patent; Ciba-Geigy Corporation; US4960787; (1990); A;,
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. 6973-09-7 name is 5-Amino-2-methylbenzenesulfonamide, 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. 6973-09-7

Example 69 5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide To a solution of Intermediate Example 13 (200 mg, 0.695 mmol) and 5-amino-2-methylbenzenesulfonamide (129.4 mg, 0.695 mmol) in isopropanol (6 ml) was added 4 drops of conc. HCl. The mixture was heated to reflux overnight. The mixture was cooled to rt and diluted with ether (6 ml). Precipitate was collected via filtration and washed with ether. HCl salt of 5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]-pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide was isolated as an off-white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1H), 8.55 (br s, 1H), 7.81 (d, J = 6.2 Hz, 1H), 7.75 (d, J = 8.7 Hz, 1H), 7.69 (m, 1H), 7.43 (s, 1H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz, 1H), 6.86 (m, 1H), 5.74 (d, J = 6.1 Hz, 1H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H), 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-2-methylbenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Novartis AG; Boloor, Amogh; Cheung, Mui; Davis, Ronda; Harris, Philip Anthony; Hinkle, Kevin; Mook, Robert Anthony Jr; Stafford, Jeffery Alan; Veal, James Martin; EP2311825; (2015); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 3144-09-0, name is Methylsulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3144-09-0

e) Boc-N-(4-Benzylsulfanyl-5-nitro-thiophen-3-ylmethyl)-methanesulfonamide Triethylamine (22.0 mL, 158 mmol), di-tert-butyl dicarbonate (27.5 g, 126 mmol), and 4-(N,N-dimethylamino)pyridine (1.28 g, 10.5 mmol) were added sequentially to a solution of methanesulfonamide (10.0 g, 105 mmol) in dichloromethane (300 mL) at 25 C. The mixture was stirred at 25 C. for 2 h, and then was concentrated in vacuo to ~40 mL volume. Ethyl acetate (350 mL) was added and the mixture was washed with 1.0 M aqueous hydrochloric acid solution (300 mL). The aqueous layer was extracted with ethyl acetate (250 mL) and the combined organic layers were dried over sodium sulfate, filtered and were concentrated in vacuo to afford Boc-N-methanesulfonamide (17.1 g, 87.6 mmol, 83%) as a white solid. 1H NMR (400 MHz, CDCl3) delta: 1.53 (9H, s), 3.27 (3H, s).

The synthetic route of 3144-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anadys Pharmaceuticals, Inc.; US2009/306057; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6292-59-7, 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.

General procedure: Sulfonamide 10a (2.0 g, 6.2 mmol, 1.1 eq) was solvedin dry THF (8 ml) and cooled to 78 ¡ãC under a nitrogen atmosphere.n-BuLi (1.62 N solution in hexane, 7.70 ml, 2.2 eq) wasadded drop-wise. After the addition was completed, the solutionwas stirred for 15 min, then the temperaturewas allowed to raise at60 ¡ãC and the THF was evaporated under very high vacuum. DMFwas added (10 ml), followed by dichloropyrimidine intermediate 9(2.0 g, 5.7 mmol, 1.0 eq) and the mixture was stirred overnight at50 ¡ãC. The reaction mixture was poured onto a 1:1 mixture ofwater-ice and the aqueous phase was washed with DEE, thenacidified with HCl and the resulting precipitate was filtrated off,washed with water and dried at 110 ¡ãC to afford a bright yellowsolid (2.22 g, yield 61.2percent).

According to the analysis of related databases, 6292-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lepri, Susan; Goracci, Laura; Valeri, Aurora; Cruciani, Gabriele; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 658 – 670;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

354-38-1, 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 354-38-1 as follows.

2-Methyl-2-(methylsulfinyl)propanenitrile (Int-3, 9.8 g, 74.7 mmol) was dissolved in dichloromethane (390 mL) at 0-5C (ice bath) and 2,2,2-trifluoroacetamide (17.0 g, 151 mmol), magnesium oxide (12.7 g, 307 mmol) and rhodium(II) acetate dimer (850 mg, 1.92 mmol) were added subsequently. Finally, a solution of iodobenzene diacetate (36.3 g, 113 mmol) in dichloromethane (98.0 mL) was added and the mixture was stirred for 1 h at 0-5C, followed by 6 h at room temperature. Then, a second portion of rhodium(II) acetate dimer (850 mg, 1.92 mmol) was added and the suspension stirred for additional 95 h at room temperature. The reaction mixture was filtered, the residue was washed with dichloromethane (100 mL) and the combined filtrate was concentrated in vacuo to afford a dark oil as crude product. After column chromatography (silica gel, 100 g, eluting with ethyl acetate / n-heptane, gradient 10:90 to 50:50) and drying in vacuo (50C, 5 mbar) the title compound was isolated as a light yellow oil, that solidified upon standing (13.74 g, 76%). HPLC (method LCMS_fglm) tR = 0.97 min. 1H NMR (CDC13, 400 MHz): delta 1.91 (s, 3 H), 1.91 (s, 3 H), 3.65 (s, 3 H). MS (ES-) m/z 241.1 [M-H] ,

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

42137-88-2, 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. 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows.

B. Dextrorotatory (+)-1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine. 57 g (0.2618 mole) of dextrorotatory (+)-(4-chlorophenyl)phenylmethylamine (prepared in Example 1.2) and 86.4 g (0.2917 mole) of N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide (prepared in Example 2.3) are added to 200 ml (1.15 mole) of ethyldiisopropylamine in a 500 ml three-necked round-bottomed flask. The mixture is heated under reflux for 3 hours, then poured in 400 ml of methanol and the mixture is cooled, in an ice bath, and stirred for 1 hour. The precipitate which forms is filtered off, washed with methanol and dried under vacuum at 50 C. 88.6 g of dextrorotatory (+)-1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine are obtained. M.P. 173.3 C. Yield: 76.7%. [alpha]D25: +43.2 (c=0.5, toluene). Optical purity: 98.35%. Analysis for C24 H25 ClN2 O2 S in %: Calc.: C 65.38 H 5.71 N 6.35 C 8.04 S 7.27 Found: 64.98 5.70 6.40 7.96 7.35

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; U C B, S.A.; US5478941; (1995); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics