Month: November 2020

109903-35-7, name is 4-Amino-N-methylbenzenemethanesulfonamide, 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. 109903-35-7

EXAMPLE 48 2,6-Dibromo-4-methylaminosulfonylmethylaniline To a stirred solution of 4-methylaminosulfonylmethylaniline (10 g) in a mixture of methylene chloride (100 mL) and methanol (200 mL) was added sodium bicarbonate (12.6 g) followed by bromine (16 g) in methylene chloride (80 mL). Then the reaction mixture was evaporated in vacuo and the residue partitioned between ethyl acetate (200 mL) and water (100 mL). The ethyl acetate phase was washed with water and brine then dried and evaporated to give the title compound as a brown solid (17.1 g). mp 155-157 C. 1 H NMR (CDCL3) delta7.4 (s, 2H), 4.6 (bs, 2H), 4.1 (m, 3H), 2.75 (d, 3H).

Statistics shows that 109903-35-7 is playing an increasingly important role. we look forward to future research findings about 4-Amino-N-methylbenzenemethanesulfonamide.

Reference:
Patent; Pfizer Inc; US5607951; (1997); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

121492-06-6, 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. 121492-06-6 name is N-Boc-(2-Aminoethyl)-N-methylamine, 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 mixture of l-(benzo[d][l,3]dioxol-5-yl)-3-(4-chloro-6-methylpyrimidin-2-yl)urea (280) (82 mg, 0.27 mmol) and 2-propanol (0.5 mL) was treated with N-(2-aminoethyl)-N- methyl carbamic acid tert-butyl ester (0.06 mL, 0.32 mmol), and triethylamine (0.06 mL, 0.40 mmol) and this was heated to 80 C with stirring overnight. Upon cooling the reaction was diluted with MeOH (3mL) and the precipitate formed was filtered to give the title compound (287) (85 mg, 72%). LC/MS: Method 4: Rt = 2.14 min, m/z = 445.3 [MH+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Boc-(2-Aminoethyl)-N-methylamine, and friends who are interested can also refer to it.

Reference:
Patent; CURTANA PHARMACEUTICALS, INC.; BEATON, Graham; TUCCI, Fabio C.; RAVULA, Satheesh B.; MCHARDY, Stanton F.; RUIZ, Francisco Xavier, III; LOPEZ, Ambrosio, Jr.; CAMPOS, Bismarck; WANG, Hua-Yu Leo; (241 pag.)WO2016/138479; (2016); 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 127-77-5 as follows. 127-77-5

General procedure: To a solution of the amine 3a-l (1 eq) in anhydrous THF (30 mL/mmol) was added4-nitrophenylisocyanate (1 eq). The reaction mixture was stirred at room temperatureovernight, concentrated. Silica cake was prepared in acetone and chromatographicseparation on silica gel (EtOAc/CH2Cl2 = 1/30 to 1/5) gave the expected compound as asolid. Compounds 4e, 4f, 4h and 4l were further recrystallized in acetone to achieve desiredpurity but with substantially lower yields.

According to the analysis of related databases, 127-77-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Xu; Ahn, Yong-Mo; Lentscher, Adam G.; Lister, Julia S.; Brothers, Robert C.; Kneen, Malea M.; Gerratana, Barbara; Boshoff, Helena I.; Dowd, Cynthia S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4426 – 4430;,
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 2675-89-0 as follows. 2675-89-0

General procedure: To a suspension of NaH (344 mg, 60% dispersion in mineral oil) in THF (17 mL) was added allyl alcohol (2) (500 mg, 8.6 mmol) at 0 C. After 1 h at the same temperature, chloroacetamide 1 (0.97 mL, 9.5 mmol) was added and the mixture was stirred for 24 h. The mixture was quenched with saturated aqueous NH4Cl and concentrated at reduced pressure. The resulting residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexanes/EtOAc, 3:1) to give 6a (1.05 g, pale yellow oil) in 85% yield.

According to the analysis of related databases, 2675-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yun, Jeong In; Kim, Hyoung Rae; Kim, Sang Kyum; Kim, Deukjoon; Lee, Jongkook; Tetrahedron; vol. 68; 4; (2012); p. 1177 – 1184;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 621-38-5, name is 3-Bromoacetanilide, A new synthetic method of this compound is introduced below., 621-38-5

Embodiment 24-methyl -2 the same-acetamido […] synthesis ofTo 10 ml reaction flask by adding 3-polybromide monoacetylaniline (0.2mmol, 42 . 81 mg), palladium acetate (0.002mmol, 0 . 45 mg), 4-methyl iodophenylamino (0.22mmol, 47 . 97 mg), K3PO4(0.6mmol, 127 . 36 mg), silver acetate (0.3mmol, 50 . 07 mg), TFA (0.1mmol) and DCE (2 ml), for 90 C reaction under the conditions, the TLC reaction monitoring, when the temperature is reduced to the room temperature, adding phenylo boric acid (1.2mmol, 29 . 26 mg) with the ligand two phenol (0.004mmol, 1 . 07 mg), 80 C to continue reaction, the end point of the detection reaction TLC. When the reaction to room temperature, add 5 ml ethyl ether, the reaction solution is poured into the separatory funnel, using 5 ml ethyl ether washing reaction bottle, and then merged into the separatory funnel in ethyl ether, is added to the separatory funnel in 10 ml saturated NaCl solution, oscillating, liquid, so then to 10 ml ¡Á 2 of ethyl ether extraction, combined with the phase, adding anhydrous sodium sulfate for drying, filtering, vacuum screwed out of the solvent, with petroleum ether and ethyl acetate 4:1(v/v) as the mobile phase, rapid column separation, get the pure product white solid 4-methyl -2 the three-acetamido […] biphenyl, yield 94.0%.

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; Heilongjiang University; Chu, Wenyi; Ren, Limin; Sun, Zhizhong; Guan, Dinghui; Han, Lu; Wang, Lulu; Shi, Yang; (10 pag.)CN104003895; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1888-91-1, The chemical industry reduces the impact on the environment during synthesis 1888-91-1, name is N-Acetylcaprolactam, I believe this compound will play a more active role in future production and life.

Further experiments, (4) and (5), were run in which N-Acetylcaprolactam wasused as the activator. In order to provide the equivalent number of labile acetyl groups to generate the peroxyacetic acid, the molar concentration of N-acetylcaprolactam was twice that of the TAED in Experiments (1) – (3) above. The results are given in Table 3 below. The results from Table 3, together with the results from column (3) of Table 1 are plotted in Figure 1. As can be seen from Figure 1, the presence of DTB results in a greater rate of generation of peroxyacetic acid.

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

Reference:
Patent; ANTEC INTERNATIONAL LIMITED; WO2006/16145; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

640-61-9, The chemical industry reduces the impact on the environment during synthesis 640-61-9, name is N,4-Dimethylbenzenesulfonamide, I believe this compound will play a more active role in future production and life.

General procedure: To a mixture of the corresponding sulfonamide (5 mmol), DMAP (0.5 mmol%)and Et3N (1.5 mL, 10 mmol) in CH2Cl2 (10 mL) was added slowly the acyl chloride made above in CH2Cl2 (10 mL) at 0C. The reaction mixture was stirred at room temperature for 2 h. Then the reaction mixture was washed with 5% HCl, brine and H2O. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure to give crude product, which was purified by column chromatography on silica gel to afford N-tosylcarboxylic amide.

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

Reference:
Article; Wang, Chen; Huang, Lingyun; Wang, Fengze; Zou, Gang; Tetrahedron Letters; vol. 59; 23; (2018); p. 2299 – 2301;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 105-60-2, name is epsilon-Caprolactam, 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. 105-60-2

A. Preparation of 3,3-Dibromoazacycloheptan-2-one To a cold solution of 45.2 g (0.4 mol) of caprolactam in CHCl3 was added 166.0 g (0.8 mol) of PCl5, keeping the temperature less than 5 C. The mixture was brought to room temperature, 2.0 g of ZnCl2 was added, and finally 128 g (0.8 mol) of bromine was added dropwise. After stirring the mixture for 5 hours at room temperature, the solvent and excess bromine was removed by vacuum distillation. The residue was poured into ice water and extracted with CH2 Cl2. The combined organic extracts were washed with sat. Na2 S2 O5, dried over MgSO4, and concentrated in vacuo to give a crude solid. Washing the solid with CH2 Cl2 /toluene yielded the product as a white powder; mp 156-159 C.

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 105-60-2.

Reference:
Patent; Nelson Research & Development Co.; US4755535; (1988); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

102-93-2, 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. 102-93-2, name is 3-Phenylpropanamide, A new synthetic method of this compound is introduced below.

EXAMPLE 13 4-(2,2-dimethyl-1-oxopropyl)-N-(3-phenylpropionyl)-benzamide A slurry of potassium hydride (from 46 grams of 35% potassium hydride in oil washed three times with hexane)in 50 ml of THF is added with stirring under nitrogen to 20 grams of 3-phenylpropionamide in 350ml of THF. After addition of the hydride is complete, the reaction is allowed to warm to room temperature and is stirred for 30 minutes. The thickened reaction mixture is cooled to 0 to 5 C. and is then added dropwise over 30 minutes to a solution of 30 grams of p-pivaloylbenzoyl chloride in 50 ml of dry THF. The resulting solution is stirred for 15 minutes at 0 to 5 C. and is then quenched with 150 ml of saturated ammonium chloride solution. The THF phase is decanted off, and the aqueous phase is extracted with ethyl acetate. The ethyl acetate extract is combined with the THF phase, dried with magnesium sulfate, filtered, and then evaporated almost to dryness. The resulting solids are triturated with ether, and the white crystals obtained are filtered, washed with ether and dried to yield the title product (m.p. 137-138 C.). When the above process is carried out using in place of the 3-phenylpropionamide, an equivalent amount of:

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; Sandoz Ltd.; US5378728; (1995); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

106984-09-2, 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. 106984-09-2, name is tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of tert-butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate (10.0 g, 34.1 mmol, Step 1 of Intermediate EN) in anhydrous THF (250 mL) was added sodium hydride (1.63 g, 40.94 mmol, 60% dispersion in mineral oil) in one portion under nitrogen atmosphere. The reaction mixture was stirred at rt for 0.5 h and thereafter it was cooled to 0 C. An 80% solution of 3-bromoprop-1-yne in toluene (5.7 mL, 51.2 mmol) was added dropwise to the reaction mixture at 0 C. over a period of 10 min. The resulting reaction mixture was stirred at 0 C. for 1 h and thereafter it was allowed to warm to rt. The resulting reaction mixture was stirred overnight at rt. Then the reaction mixture was quenched with a small aliquot of methanol (1.6 mL) and concentrated on a rotary evaporator. The obtained crude material was suspended in DCM (100 mL) and was washed with water (2¡Á30 mL) and brine (50 mL). The resulting organic layer was dried over anhydrous sodium sulphate, filtered and concentrated on a rotary evaporator. The obtained crude product was purified by silica gel chromatography (gradient Ethyl acetate/Hexanes) to give the title compound (6.25 g, 55%) as a light yellow viscous liquid.

The synthetic route of 106984-09-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics