Month: February 2021

Application of 16375-88-5, 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. 16375-88-5, name is N-(4-(Hydroxymethyl)phenyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. (4-Acetamido)-phenylmethyl-4-nitrophenylcarbonate To a solution of 242.8 mg of p-nitrophenyl chloroformate in 5 mL of acetonitrile at 0 C. was added sequentially, 165.2 mg of 4-acetamidobenzyl alcohol and 0.13 mL of 4-methyl morpholine. The mixture was stirred for 24 hours and concentrated in vacuo. The residue was taken up in CH2 Cl2 and washed with 5% sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 320 mg of the title compound. TLC: Rf=0.23, 50% EtOAc/hexane.

The synthetic route of N-(4-(Hydroxymethyl)phenyl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals, Incorporated; US5783701; (1998); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 618-48-4, name is 3-Chlorobenzamide, 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. Recommanded Product: 618-48-4

Then slowly raise the temperature, turn on the ultrasonic generator at the same time, control the ultrasonic frequency of 20KHz, the concentrated ultrasonic horn is directly immersed in the reaction liquid of the kettle body, and a large amount of energy is directly transmitted to the reaction medium.Effectively convert electrical energy into ultrasonic energy, and control the size of ultrasonic energy by changing the amplitude of the generator. Use a constant temperature system to make the material react at a constant temperature of 230 ~ 250 C for 2h, and then continue to increase the temperature, control the temperature of 250 ~ 270 C, and react for 2h. To generate a mixture containing m-chlorobenzonitrile, turn off the ultrasonic generator.Crude nitrile was distilled off from the mixture containing m-chlorobenzonitrile under reduced pressure, and the residue after distillation contained intermediate products (ammonium m-chlorobenzoate and m-chlorobenzamide) produced by the reaction, which were left in the ultrasonic thermostat and continued at the next feeding reaction.The crude nitrile is washed with water, filtered, dried and then distilled under reduced pressure to obtain the finished product. The content of m-chlorobenzonitrile measured by high performance liquid chromatography was 97.0%. Calculate the yield. Based on m-chlorobenzoic acid, the yield of finished m-chlorobenzonitrile is 92.5%.The wastewater produced by washing the crude nitrile with water contains available raw materials m-chlorobenzoic acid, the intermediate products ammonium m-chlorobenzoate, and m-chlorobenzamide. The water is recovered by distillation and concentration, and the intermediate products are recovered. After drying, During the secondary reaction, it was put into the reaction kettle as part of the raw materials to continue the reaction.

The synthetic route of 3-Chlorobenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sanmenxia Huanyu Biochemical Technology Co., Ltd.; Duan Jingjie; Zhang Weimin; Liang Zhenxian; Wei Zhanyong; Tan Jing; Zhang Kun; Wang Xinyue; Wang Yan; Wang Zhiquan; (7 pag.)CN110467541; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 5202-85-7, A common heterocyclic compound, 5202-85-7, name is 2-Amino-5-chlorobenzamide, molecular formula is C7H7ClN2O, 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.

An aromatic amine 1q-1 (0.20 mmol) and a platensimycin acid (0.10 mmol) were weighed.2-(7-Azobenzotriazole)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU) (0.30 mmol) was added to the reaction flask and 1.0 ml was added.N,N-dimethylformamide, stirring at room temperature; slowly adding triethylamine (0.45 mmol), stirring for 12 hours, rotary evaporationSolvent to obtain a crude product, which is subjected to column chromatography to obtain a platensimycin analog2q-1, yield 46%.

The synthetic route of 5202-85-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changsha Tianci Bio-pharmaceutical Technology Co., Ltd.; Changsha Cihang Pharmaceutical Institute Co., Ltd.; Ha Yao Cihang Pharmaceutical Co., Ltd.; Duan Yanwen; Shen Ben; Huang Yong; Zhu Xiangcheng; Qiu Lin; Tian Kai; (39 pag.)CN107793388; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 5004-88-6, These common heterocyclic compound, 5004-88-6, name is 2-Amino-4,5-dimethoxybenzamide, 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 stirred mixture of 4 g of 2-amino-4,5-dimethoxybenzamide and 200 ml of ether was added dropwise, e solution of 3.3 g of benzoyl isothiocyanate in 100 ml of ether over 15 minutes. After 24 hours, the solid was collected, giving 7 g of the desired product as white crystals, mp 204-207 C. (dec.).

Statistics shows that 2-Amino-4,5-dimethoxybenzamide is playing an increasingly important role. we look forward to future research findings about 5004-88-6.

Reference:
Patent; American Cyanamid Company; US5001157; (1991); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 90-16-4, These common heterocyclic compound, 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, 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.

A solution of l,2,3-benzotriazin-4(3H)-one (commercially available, 1.0 equiv.), 2- chloromethyl-oxirane (4.0 equiv.) and potassium carbonate (4.0 equiv.) in methyl ethyl ketone was refluxed for about 16 hours. The reaction mixture was concentrated under vacuum; the residue was taken in water and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography using mixture of ethyl acetate and hexane as eluent to form 3- (oxiran-2-ylmethyl)-l,2,3-benzotriazin-4(3H)-one. Yield: 75%

The synthetic route of 90-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/117760; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 112257-19-9, 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. 112257-19-9 name is tert-Butyl methyl(2-(methylamino)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.

Step 6 tert-Butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate A mixture of 3-iodo-1-(oxan-2-yl)-1H-pyrazole-4-carbaldehyde (21.5 g, 70.24 mmol, 1.00 equiv), tert-butyl N-methyl-N-(2-(methylamino)ethyl)carbamate (20 g, 106.23 mmol, 1.51 equiv) and NaBH(OAc)3 (29.8 g, 137.98 mmol, 1.96 equiv) in dichloroethane (300 mL) was stirred for 1 h at room temperature. The reaction was diluted with 300 mL of dichloromethane and then washed with 3*300 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-7percent methanol in dichloromethane to give 31 g (92percent) of tert-butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate as a yellow oil. 1H NMR (300 MHz, CDCl3): delta 7.62 (s, 1H), 5.34-5.30 (m, 1H), 4.06-4.02 (m, 1H), 3.68-3.62 (m, 1H), 3.42-3.38 (m, 4H), 2.85 (s, 4H), 2.62-2.53 (m, 2H), 2.47-2.46 (m, 2H), 2.13-1.97 (m, 3H), 1.74-1.69 (m, 3H), 1.46 (s, 9H) ppm. LCMS (method A, ESI): RT=1.17 min, m/z=479.0 [M+H]+.

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

Reference:
Patent; Epizyme, Inc.; Mitchell, Lorna Helen; Shapiro, Gideon; Chesworth, Richard; Moradei, Oscar Miguel; US2014/288128; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 224789-21-3, 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 224789-21-3 as follows.

Example 5 Preparation of 2-(2-ethoxy-5-chlorosulfonyl)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][ 1,2,4]triazine-4-one Chlorosulfuric acid (50ml)was added into a 100ml three-neck flask with a stirrer, 2-(2-ethoxy)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][1,2,4]triazine-4-one (31.2g (0.1mol))was added in batches under stirring in an ice bath. The reaction was exothermic and was performed for 12 hrs. The reaction solution was slowly poured into icy water (100g), a white solid was separated out, filtered, dried. A white solid (30g)was obtained with a yield of 76%.

According to the analysis of related databases, 224789-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Dade Pharmaceutical Group Co., Ltd.; WANG, Jianping; WANG, Jianguo; EP2666776; (2013); 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 402-46-0 as follows. name: 4-Fluorobenzenesulfonamide

General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 C, and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 ¡Á 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).

According to the analysis of related databases, 402-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Luo, Yin; Qiu, Ke-Ming; Lu, Xiang; Liu, Kai; Fu, Jie; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4730 – 4738;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 32428-71-0, name is 2-Chloro-N-(2-ethyl-6-methylphenyl)acetamide, 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 32428-71-0, Formula: C11H14ClNO

A. 1-[(2-Ethyl-6-methylphenyl)carbamoylmethyl]-2-methyl-2-imidazoline. In a manner similar to Ex. IA react 21.17 gm. (0.1 M) of 2-chloro-2′-ethyl-6′-methylacetanilide and 42.1 gm. (0.5 M) of lysidine in 250 ml. of nitromethane, to obtain the title compound: NMR (CDCl3): delta=1.16(t,3), 1.97(s,3), 2.18(s,3), 2.54 (q,2), 3.10-3.70(m,4), 3.87(s,2), 7.15 (s,3) and 8.78(bs,1)ppm.

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; Berlex Laboratories, Inc.; US4353921; (1982); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 147751-16-4, name is tert-Butyl methylsulfonylcarbamate, molecular formula is C6H13NO4S, 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: tert-Butyl methylsulfonylcarbamate

Example 243: t-ButylN-[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methylbutyl]-N-methylsulfonylcarbamate The 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methyl-1-butanol (97.2 mg, 0.259 mmol) obtained in Example 239, t-butyl N-methylsulfonylcarbamate (101 mg, 0.518 mmol) and triphenylphosphine (138 mg, 0.518 mmol) were dissolved in tetrahydrofuran (3 ml), followed by the addition of diisoopropyl azodicarboxylate (102 mul, 0.518 mmol) at room temperature.. The reaction mixture was stirred at room temperature for 18 hours.. The reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of ammonium chloride, water and brine, dried over magnesium sulfate and then concenetrated.. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=3:2 elude was concentrated, whereby the title compound (136 mg, 0.246 mmol, 95%) was obtained as a colorless amorphous substance.1H-NMR (400 MHz, CDCl3) delta: 1.33(3H,d,J=6.8Hz), 1.35-1.45(1H,m), 1.52(9H,s), 1.99-2.08(1H,m), 2.70-2.78(1H,m), 3.27(3H,s), 3.65-3.76(2H,m), 4.45(1H,d,J=7.6Hz), 6.77(1H,td,J=9.0,4.6Hz), 6.91-6.97(1H,m), 7.32(2H,d,J=8.5Hz), 7.38-7.45(1H,m), 7.50(2H,d,J=8.5Hz). MS m/z: 552 (M++H), 574 (M++Na). FAB-MS: 552.1070 (Calcd for C23H29ClF2NO6S2: 552.1093), 574.0875 (Calcd for C23H28ClF2NO6S2Na: 574.0912).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 147751-16-4, its application will become more common.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics