Author: Jessica.F

Reference of 782-45-6, 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. 782-45-6 name is 4-Amino-N-phenylbenzamide, 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: A solution of triphosgene (1 eq) in 5 mL dry THF was cooled to -78C. A solution of 4-(4-morpholin-4-yl-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine HCl salt (3 eq) and N,N-diisopropylethylamine (4.8 eq) in dry THF (5 mL) was added dropwis to the triphosgene solution. The mixture was warmed to room temperature and stirred for 50 min. A solution of the second amine (3 eq.) and N,N-diisopropylethylamine (2.5 eq) in dry THF (5 mL) was added dropwise. The reaction mixture was stirred for 48-72 h. The solvent was removed under reduced pressure then saturated aqueous sodium bicarbonate solution (5 mL) was added to the residue to neutralize any acid. Then the solvent was removed under reduced pressure. The crude product was dissolved in 3 mLof DMSO, filtered and purified reversed phase HPLC (15 min gradient acetonitrile in water, 0.1% trifluoroacetic acid or formic acid as a m odifier).The pure product was obtained as trifluoroacetate or formate salt.

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

Reference:
Article; Al-Ashmawy, Aisha A.K.; Ragab, Fatma A.; Elokely, Khaled M.; Anwar, Manal M.; Perez-Leal, Oscar; Rico, Mario C.; Gordon, John; Bichenkov, Eugeney; Mateo, George; Kassem, Emad M.M.; Hegazy, Gehan H.; Abou-Gharbia, Magid; Childers, Wayne; Bioorganic and Medicinal Chemistry Letters; vol. 27; 14; (2017); p. 3117 – 3122;,
Amide – Wikipedia,
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Reference of 2895-21-8, These common heterocyclic compound, 2895-21-8, name is N-Isopropyl-2-chloroacetamide, 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.

To a solution of 2-chloro-N-isopropylacetamide (201 mg, 1.48 mmol) in ethanol (1.73 mL) was added 4-bromo-o-anisidine (300 mg, 1.48 mmol) and potassium carbonate (615 mg, 4.45 mmol). The reaction mixture was then allowed to stir at 80 C overnight. The reaction was cooled to r.t. and concentrated under reduced pressure. The residue was taken up in EtOAc, and washed with NaOH (4.0 M). The aqueous layer was extracted with EtOAc (x3), the organic layers combined, washed with saturated brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography eluting with 30-50% acetonitrile (0.1% formic acid additive) in water (0.1% formic acid additive) to yield 2-(4-bromo-2-methoxy-anilino)-N-isopropylacetamide (110 mg, 0.36 mmol, 25% yield) as a white solid. UPLC-MS (ES+, Method A): 1.65 min, m/z 301.2 [M+H]+.1H NMR (400 MHz, CDCl3) delta6.98 (dd, J = 8.3, 2.7 Hz, 1H), 6.90 (d, J = 2.0 Hz, 1H), 6.47-6.41 (m, 1H), 6.34 (d, J = 8.3 Hz, 1H), 4.18-4.08 (m, 1H), 3.87 (s, 3H), 3.73 (s, 2H), 1.11 (d, J = 6.6 Hz, 6H).

The synthetic route of 2895-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
Amide – Wikipedia,
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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. 108448-77-7, name is (1R)-(+)-2,10,Camphorsultam belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: (1R)-(+)-2,10,Camphorsultam

EXAMPLE 3; (E)-3-Benzyloxypropenoyl-(2’S)-bornane-10,2-sultam (Scheme 3, 3-3); To a solution of (E)-3-benzyloxyacrylic acid (1.74 kg, 9.88 mol) and dichloromethane (20 L) is added thionyl chloride (1.75 kg, 14.7 mol) over a period of 30 min. The reaction mixture is heated at reflux and the SO2 and HCl generated are scrubbed through a solution of aqueous NaOH. After 4 h (reaction progress is monitored by 1H NMR analysis), the solvent is removed under vacuum and the residual thionyl chloride is removed under vacuum overnight to give 2.00 kg (104%) of the desired acid chloride 3-2. To a solution of camphor sultam (1.72 kg, 7.98 mol) in THF (16 L) at -40 C. is added methyl magnesium bromide (2.79 L, 8.38 mol; 3M solution in ether) at a dropwise rate while maintaining the internal temperature between -30 C. and -40 C. The reaction mixture is stirred for an additional hour at 40 C. To the anion at -40 C. is added slowly, acid chloride 3-2 (1.92 kg, 96% purity based upon the use of acid, 9.4 mol) in THF (8 L) while maintaining the internal temperature below -25 C. The reaction mixture is further stirred between -30 C. and -40 C. for 1 h and allowed to warm to +10 C. over a period of 5-6 h. The reaction mixture is then quenched with saturated aqueous NH4Cl (16 L). The aqueous layer is separated and extracted twice with ethyl acetate (10 L). The combined organic layers are washed with saturated aqueous sodium carbonate (20 L) and brine (20 L). The organic layer is filtered through a pad of anhydrous MgSO4 and concentrated under vacuum to dryness to furnish 3.12 kg of the crude product 3-3. The crude product is taken up in ethyl acetate (8.3 L) and heated to 60 C. to dissolve the crude residue. The homogenous solution is diluted slowly with hexanes (30 L) while maintaining the solution at reflux. The reaction mixture is kept in a cold room for 16 h at 4 C. The crystalline material that separated is collected by filtration and washed with hexanes to give 1.906 kg (60%) of the desired product 3-3. The filtrate also contains the product, but no attempts are made to recover this material from the filtrate.

The synthetic route of 108448-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BioCryst Pharmaceuticals, Inc.; US2006/128789; (2006); A1;,
Amide – Wikipedia,
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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. 14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, A new synthetic method of this compound is introduced below., name: 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide

Add dU-I (0.7mmol, 247mg) to a single-mouth bottle, add 9.7mg CuI and 20.3mg Pd(PPh3)4 to the reaction flask, vacuum, protect with nitrogen, wrap with aluminum foil, add 2.3ml DMF, stir and dissolve. 0.2 ml of TEA was added, and trifluoroethylpropynylamine (254 mg, 1.7 mmol) was weighed and dissolved in DMF, and then added to the above reaction flask, stirred at room temperature, and allowed to react overnight. After the reaction is completed, the solvent is evaporated to dryness under reduced pressure, and then directly separated by column chromatography, and dichloromethane and methanol are mixed at a volume ratio of 20:1 as a leaching agent to obtain dU-F3.

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; Suzhou Bai Yuan Genes Co., Ltd.; Lanzhou Bai Yuan Genes Co., Ltd.; Che Tuanjie; (40 pag.)CN108752406; (2018); A;,
Amide – Wikipedia,
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Some common heterocyclic compound, 84713-20-2, name is Benzyl vinylcarbamate, molecular formula is C10H11NO2, 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. Recommanded Product: Benzyl vinylcarbamate

EXAMPLE 3 cis-(2-Ethyl-6-trifluoromethyl-1 2,3,4-tetrahydro-quinolin-4-yl)-carbamic Acid Benzyl Ester A one liter, four neck flask under nitrogen atmosphere was charged with N-vinyl-carbamic acid benzyl ester (27.66 g, 156 mmol, 1.0 equiv) and dry toluene (500 mL). (1-Benzotriazol-1-yl-propyl)-(4-trifluoromethyl-phenyl)-amine (50.0 g, 156 mmol, 1.0 equiv) and p-toluenesulfonic acid monohydrate (297 mg, 1.56 mmol, 0.01 equiv) were added, and the mixture heated to 70 C. After 2 h, the mixture was cooled to room temperature and transfered to a separatory funnel. Ethyl acetate (500 mL) was added. The mixture was washed 1*200 mL 1N NaOH, 1*200 mL H2O, 1*200 mL brine, and dried (MgSO4). The mixture was filtered and the solids washed 1*50 mL ethyl acetate. The filtrate was concentrated to approximately 250 mL. 500 mL toluene were added, and the mixture concentrated to approximately 500 mL. 500 mL n-heptane were added, the slurry was stirred 1 h, filtered through a Buchner funnel, and dried. cis-(2-Ethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid benzyl ester was isolated as a white powder (45.04 g, 76%): mp 155-157 C.; 1H NMR (DMSO-d6, 400 MHz) delta 0.92 (t, 3H, J=7.5 Hz), 1.5 (m, 3H), 2.00 (m, 1H), 3.35 (m, 1H), 4.77 (m, 1H), 5.07 (d, 1H, J=12.5 Hz), 5.15 (d, 1H, J=12.5 Hz), 6.35 (s, 1H), 6.61 (d, 1H, J=8.5 Hz), 7.12 (s, 1H), 7.18 (dd, 1H, J=1.9, 8.5 Hz), 7.4 (m, 5H), 7.70 (d, 1H, J=9.1 Hz); 13C NMR (DMSO-d6, 100 MHz) delta 157.03, 149.02, 137.79, 128.82, 128.23, 128.03, 125.9 (q, J=270 Hz), 125.06, 123.50, 121.73, 115.2 (q, J=31.7 Hz), 113.33, 65.85, 52.09, 47.83, 34.02, 28.68, 9.93; DEPT spectrum: quaternary carbons delta 157.03, 149.02, 137.79, 125.9, 121.73, 115.2; CH carbons delta 128.82, 128.23, 128.03, 125.06, 123.50, 113.33, 52.09, 47.83; CH2 carbons delta 65.85, 34.02, 28.68; CH3 carbon delta 9.93; IR (drifts) 3430 (m), 3303 (s), 2951 (m), 1686 (vs), 1542 (vs), 1088 (vs); MS (APCI+) m/z (rel. intensity) 379 (M+H+, 53), 228 (100); Anal. Calcd for C20H21N2O2F3: C, 63.48; H, 5.59; N, 7.40; Found: C, 63.69; H, 6.06, N, 7.36.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 84713-20-2, its application will become more common.

Reference:
Patent; Shear, Charles L.; US2002/35125; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 627-12-3, 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. 627-12-3, name is Propyl carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 ¡Á 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

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, Propyl carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
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Amide – an overview | ScienceDirect Topics

Application of 214210-30-7, 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. 214210-30-7, name is 4-Bromo-2-fluorobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Sodium ethoxide (0.546 mL, 6.61 mmol) is dissolved in DMF (11 mL.). 4-Bromo-2- fluorobenzenesulphonamide (1.20 g, 4.72 mmol ) in DMF (5 mL) is added dropwise. The RM is stirred at RT for 1 h, then the temperature is raised to 60 C for 2h. Sodium ethoxide (0.39 mL, 4.72 mmol) is added and the RM is stirred for another hour. The RM is partitioned between EtOAc and water. The organic phase is washed with water and brine, dried over MgSC , filtered and evaporated under reduced pressure. The crude is purified by FC (H/EtOAc from 0:100 to 50:50), to afford the title compound as a white powder (841 mg, 64%). LC-MS A: tR = 0.78 min; no ionization.

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-Bromo-2-fluorobenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; FRETZ, Heinz; LYOTHIER, Isabelle; POTHIER, Julien; RICHARD-BILDSTEIN, Sylvia; SIFFERLEN, Thierry; WYDER PETERS, Lorenza; POZZI, Davide; CORMINBOEUF, Olivier; (306 pag.)WO2017/85198; (2017); A1;,
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Amide – an overview | ScienceDirect Topics

Reference of 72505-21-6, 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. 72505-21-6, name is 4-(Trifluoromethyl)thiobenzamide, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-(trifluoromethyl)benzothioamide 1 (10 mmol/2.05 g) in the minimum required quantity of absolute ethanol (10 mL), ethyl 2-chloroacetoacetate 2 (15 mmol/2.46 g) was added and the resulting mixture was heated on the water bath for 5 h. The solution was cooled down and neutralized with a solution of potassium carbonate. The resulting solid was filtered, washed with water, recrystallized from ethanol to give the target compound.

The chemical industry reduces the impact on the environment during synthesis 4-(Trifluoromethyl)thiobenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nastasa, Cristina; Tiperciuc, Brindusa; Duma, Mihaela; Benedec, Daniela; Oniga, Ovidiu; Molecules; vol. 20; 9; (2015); p. 17325 – 17338;,
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Adding a certain compound to certain chemical reactions, such as: 103361-99-5, name is 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, 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 103361-99-5, HPLC of Formula: C8H6FNO2

To a solution of 7-fluoro-4H-benzo[1,4]oxazin-3-one (3.00 g, 17.95 mmol) in concentrated H2SO4 (12 mL) at -10 C. was added a mixture of fuming nitric acid (1.131 g, 17.95 mmol, 0.75 mL) and concentrated H2SO4 (0.75 mL) dropwise, keeping the internal temperature below 0 C. After addition, the reaction mixture was stirred at -10 C. for 10 min. The reaction mixture was poured onto crushed ice (200 g) with care. The precipitate was collected by filtration, washed with water (50 mL) and dried in vacuo to give 7-fluoro-6-nitro-4H-benzo[1,4]oxazin-3-one as a light yellow solid (3.5 g, 92%). 1H NMR (DMSO-d6, 400 MHz): delta 11.02 (s, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.23 (d, J=12.0 Hz, 1H), 4.77 (s, 2H).

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; Wang, Jianfei; Breinlinger, Eric C.; Barth, Martine; Friedman, Michael M.; Guillier, Fabrice; Argiriadi, Maria A.; Edmunds, Jeremy; Potin, Dominique; Hobson, Adrian D.; Wu, Wentao; Bonafoux, Dominique; Thomas, Didier; George, Dawn M.; Dai, Linlin; Zhang, Yang; US2014/206663; (2014); A1;,
Amide – Wikipedia,
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Reference of 758-96-3, 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. 758-96-3 name is N,N-Dimethylpropionamide, 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.

Weigh 4-methylbenzothiazole (0.5mmol, 75mg), K2S2O8 (2mmol, 0.54g) and Eosin Y (0.01mmol, 6.5mg) in a 25mL Schlenk reaction tube,Then add N, N-dimethylpropionamide (38mmol, 3.8g), put it under the LED white light of 20W power to react, stir the reaction at room temperature, monitor the progress of the reaction with TLC, the reaction ends after 24h, and the reaction solution is concentrated The solvent was removed, and the concentrated solution was separated by column chromatography (eluent: petroleum ether / ethyl acetate with a volume ratio of 5: 1) to obtain a yellow oil, that is, the derivative Im. The yield was 72%.

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

Reference:
Patent; Zhejiang University of Technology; Weng Jianquan; Xu Wenxiu; Dai Xiaoqiang; Liu Xinghai; (11 pag.)CN110432282; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics