Category: amides-buliding-blocks

These common heterocyclic compound, 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide, 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. 144-80-9

General procedure: To a stirred solution of sulphonamide (2 mmol),chloroacetylchloride (2 mL) and try ethylamine (0.1 mL)in dry dimethylformamide at 0-5 oC, aminochalcone 1d-1f (2 mmol) was added and stirred at room temperature for3-4 hours by a magnetic stirrer. The stirred reaction mixturewas then refluxed for 8-9 hours. The reaction was monitoredby TLC. After the completion of the reaction, the reactionmixture on hot was poured to crushed ice afforded precipitatesof chalcone-sulphonamide hybrids 3a-6f. Precipitatesthen washed with cold aqueous sodium carbonate and thecrude product was recrystallized in acetone.

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 144-80-9.

Reference:
Article; Khanusiya, Mahammadali; Gadhawala, Zakirhusen; Journal of the Korean Chemical Society; vol. 63; 2; (2019); p. 85 – 93;,
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640-61-9, 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. 640-61-9, name is N,4-Dimethylbenzenesulfonamide, A new synthetic method of this compound is introduced below.

To a solution of bromoethynylbenzene (1.4 g, 8.0 mmol) in 24 mL of anhydrous toluene in a reaction vial were added methyl phenylcarbamate (1.5 g, 9.6 mmol), K3PO4 (3.4 g, 16 mmol), copper sulfate-pentahydrate (400 mg, 16 mmol), and 1,10-phenanthroline (577 mg, 3.2 mmol). The reaction mixtures was capped under an argon atmosphere, and heated in an oil bath at 80 ?C for 15 h. The progress of the reaction was monitored using TLC analysis. Upon completion, the reaction mixture was allowed to cool to room temperature, and diluted with 15 mL of ethyl acetate. The mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The crude residue was purified by column chromatography with eluent of Hexane/ ethyl acetate = 19/1 to give 1.6 g of 1 in 80 % yield as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.55 (dd, J = 1.2, 8.6 Hz, 2H), 7.45-7.40 (m, 4H), 7.33-7.28 (m, 4H), 3.92 (s, 3H). 13C NMR. (100 MHz, CDCl3) delta 154.9, 139.7, 131.5, 129.1, 128.4, 128.0, 127.2, 124.8, 123.0, 83.0, 70.3, 54.5.

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; Sato, Akihiro H.; Ohashi, Kazuhiro; Iwasawa, Tetsuo; Tetrahedron Letters; vol. 54; 10; (2013); p. 1309 – 1311;,
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7341-96-0, A common compound: 7341-96-0, name is Propiolamide, 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 6; Synthesis of compound (I): 1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxyamide (Rufinamide) A 500 ml round-bottom flask is loaded with 2,6-difluorobenzyl azide (100 g, 0.59 mole) dissolved in methanol (300 ml), then propiolamide (49 g, 0.71 mole) obtained according to Example 5 is added under stirring to obtain a solution. Afterwards, CuSO4 pentahydrate (1.46 g, 5.9 mmoles) and ascorbic acid (5.19 g, 29.6 mmoles) are added in succession. The reaction mixture spontaneously reaches 40C and is kept under stirring for 4 hours at the same temperature. The formed solid is then filtered off, washed with methanol and water, and dried in an oven at 50C, thereby affording 133 g of a solid crude in 89% yield. The solid is suspended in water (300 ml), the suspension is treated with 33% aqueous ammonia (50 ml) and left under stirring for 3 hours, then the resulting white solid is filtered and dried in an oven. 130 g of a crystalline solid are obtained in 87% yield. 1H NMR (400 MHz, DMSO-d6), delta ppm: 8.56 (s, 1 H), 7.87 (bs, 1H), 7.60-7.43 (m, 2H), 7.20 (m, 2H), 5.72 (s, 2H).

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, Propiolamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dipharma Francis S.r.l.; EP2230234; (2010); A1;,
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2623-33-8, 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 2623-33-8 as follows.

General procedure: A 10 mL Schlenk tube equipped with a magnetic stirrer was charged with [Rh Cp* Cl2]2 (5 mol%), AgSbF6 (20 mol%), Cu(OAc)2 (1equiv), Ag2CO3(1equiv),and substituted acetanilideas 1 (0.2 mmol). The tube wasevacuated and backfilled with argon for three times. Then allyl carbonate (0.4 mmol) in dioxane (1 mL) was added. After addition of all substrates, the reactionmixture was stirred and heated at 110Cfor 24h. Then reaction was cooled to room temperature. Solvent and volatile reagents were removed by rotary evaporation and theresidue was purified by flash column chromatography on silica gel to give the target product

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

Reference:
Article; Gong, Tian-Jun; Cheng, Wan-Min; Su, Wei; Xiao, Bin; Fu, Yao; Tetrahedron Letters; vol. 55; 11; (2014); p. 1859 – 1862;,
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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. 621-38-5, name is 3-Bromoacetanilide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 621-38-5

Example 4; Example 3 is repeated under the same conditions except that 2% millimolar of (PdAllylCl)2 is used instead of Pd(OAc)2. The reaction is always conducted at 90C. The same product of example 3 is obtained with 84% molar yield.

The synthetic route of 621-38-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F.I.S. Fabbrica Italiana Sintetici S.p.A.; EP2433931; (2012); A1;,
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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 7803-58-9 as follows. 7803-58-9

4-{4-(2,4-Dichloro-phenyl)-2-[2-(3′-methanesulfonyl-biphenyl-4-yl)-(E)-vinyl]-imidazol-1-yl}-benzaldehyde (700 mg, 1.22 mmol)) was cyclized according to general procedure AB to provide (+/-)-4-(4-{4-(2,4-dichloro-phenyl)-2-[2-(3′-methanesulfonyl-biphenyl-4-yl)-(E)-vinyl]-imidazol-1-yl}-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-ylideneamine (210 mg, 25% yield). LCMS: m/z 678 (M+H)+. 1H NMR (DMSO-d6, 400 MHz): delta 3.31 (s, 3H), 5.52 (d, 1H), 6.94 (d, 1H), 7.57 (dd, 1H), 7.66-7.74 (m, 7H), 7.76-7.82 (m, 3H), 7.88 (d, 1H), 7.92 (m, 1H), 8.06 (m, 1H), 8.09 (s, 1H), 8.18 (m, 1H), 8.31 (d, 1H), 8.42 (br s, 1H) ppm.; General Procedure AB: Preparation of C-sulfahydantoin Derivatives To a suspension of aryl aldehyde in ethanol (0.1-0.5 M) was added sodium cyanide (20 eq) and sulfamide (10 eq). The mixture was heated at reflux under nitrogen for 18 hours. The mixture was then diluted with aqueous NaHCO3/EtOAc and the layers were separated. The aqueous layer was washed with EtOAc and the combined organic layers were washed with water and brine, then dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography to afford the iminosulfahydantoin derivative.

According to the analysis of related databases, 7803-58-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mjalli, Adnan M.M.; Polisetti, Dharma R.; Subramanian, Govindan; Quada, James C.; Arimilli, Murty N.; Yarragunta, Ravindra R.; Andrews, Robert C.; Xie, Rongyuan; US2005/187277; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 631-58-3, name is Propanethioamide, 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 631-58-3, 631-58-3

Reference Example L 26 2-ethyl-5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazole A solution of 2-bromo-2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone hydrobromide (11 g, 29 mmol) and thiopropionamide (2.7 g, 30 mmol) in N,N-dimethylformamide (30 mL) was stirred at room temperature for 14 hrs. Aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate = 4: 1) to give the title compound (3.3 g, yield 38%). oil 1H-NMR(CDCl3)delta: 1.64 (3H, t, J= 7.6Hz), 2.34 (3H, s), 3.10 (2H, q, J= 7.6Hz), 6.84-6.86 (1H, m), 7.05-7.09 (1H, m), 7.13-7.25 (3H, m), 7.37 (1H, s), 8.10 (1H, d, J= 5.6Hz).

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, Propanethioamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1402900; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 4093-29-2, name is Methyl 4-acetamido-2-methoxybenzoate, 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 4093-29-2. 4093-29-2

[0543] To a solution of 269-3 (4.46 g, 20 mmol), PdOAc (0.45 g, 2 mmol) and Cu(OAe)2 (7.26 g, 40 mmol) in 1.2-dichloroethane ( 150 mL) was added anhydrous CuBr2 (8.93 g. 40 mmol) under N2 atmosphere. The mixture was stirred at 90 C for 72 h. After cooling to r.t., the reaction was quenched by water, and filtered through a celite pad. The solution was washed with brine, dried by anhydrous Na2S04 and concentrated at low pressure. The residue was purified by flash column chromatography on silica gel (PE:EA 1 : 1 ) to give 269-4 (6.04 g, 51 .3%). +ESI-MS:m/z 303.7 [M+I I]

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 Methyl 4-acetamido-2-methoxybenzoate.

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); A1;,
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1746-77-6, These common heterocyclic compound, 1746-77-6, name is Isopropyl carbamate, 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.

Intermediate 491 -methylethyl (2E)-2-butenoylcarbamateIsopropyl carbamate (30 g, 291 mmol, available from TCI) was charged to a 3L Lara vessel and dry Tetrahydrofuran (THF) (150 ml) added. (2E)-2-butenoyl chloride (31.2 ml, 326 mmol, available from Aldrich) was added under nitrogen and the jacket cooled to – 30C. When the solution temperature reached -17C 1 M Lithium tert-butoxide (655 ml, 655 mmol) was added by peristaltic pump over 2 hours, keeping the reaction temperature between -10C and -18C. Once the addition was complete the mixture was complete the mixture was stirred for 30 mins and brought to 0C. Diethyl ether (450ml) and 1 M HCI (375ml) were added and the mixture brought to 20C with vigourous stirring. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. Brine (375ml) was added and the mixture stirred vigourously. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. The organic layer was dried (magnesium sulfate), filtered and evaporated to a brown oil (60g). The mixture was loaded on to a 40+M Biotage silica column and eluted with DCM:ethyl acetate (1 :1 to 0:1 , 10CV). The product containing fractions were evaporated to dryness and loaded on to a 1500g Redisep Isco silica column and eluted with a gradient of 0 to 40% ethyl acetate in cyclohexane. The clean, product containing fractions were evaporated to an off white solid (15.41 g). LCMS (Method C): Rt = 0.68 , MH+ = 172

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 1746-77-6.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); 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. 4664-01-1 name is 3,4-Pyridinedicarboximide, 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. 4664-01-1

NaOH (10% aqueous, 640 ml) was cooled to 7 C. and bromine (15 ml, 286.82 mmol) added dropwise. Pyrrolo[3,4-c]pyridine-1,3-dione (41.711 g, 281.6 mmol) was then added to the reaction mixture before it was heated to 80 C. for 30 minutes. After this time the reaction was allowed to warm to 37 C. and the pH modified to 5.5 by the addition of acetic acid (70 ml). A suspension formed that was removed by filtration and washed with 20 ml of ice cold methanol to give the title compound (26.58 g, 68.33%) in a suitably clean form to be used without any further purification. m/z (LC-MS, ESP): 139 [M+H]+, R/T=0.72 mins.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4-Pyridinedicarboximide, and friends who are interested can also refer to it.

Reference:
Patent; Kudos Pharmaceuticals Ltd; US2006/199804; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics