Category: amides-buliding-blocks

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,
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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;,
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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

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,
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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 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,
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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 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

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;,
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Amide – an overview | ScienceDirect Topics

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

A common heterocyclic compound, 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, molecular formula is C10H15NO2S, 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. 6292-59-7.

A mixture of 4-teritary butyl benzene sulfonamide (15.2 grams) having 0.11percent of 4-isopropyl benzene sulfonamide, potassium carbonate (19.77 grams), tetrabutylammonium bromide (0.7 grams) in toluene (750 ml) was heated to 45-50¡ãC and stirred for 30 minutes.4,6-dichloro-5-(2-methoxyphenoxy)-2,2′-bipyrimidine (25 grams) was added the above mixture and heated to reflux temperature then stirred for 12 hours. The reaction mixture was cooled and then quenched with water. The reaction mixture was filtered and washed the solid with water. Acetonitrile (300 ml) was added to wet solid and heated to reflux temperature then stirred for 2 hours. Water (50 ml) was added to the above wet solid and acidified with hydrochloric acid. The solid was filtered, washed with water and dried to get the title compound.Yield: 80 grams; Purity by HPLC: 98.97 percent; isopropyl derivative: 0.11percent

The synthetic route of 4-(tert-Butyl)benzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; ESWARAIAH, Sajja; VENKAT REDDY, Ghojala; WO2011/21216; (2011); A2;,
Amide – Wikipedia,
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711007-44-2, Name is 2,3-Diaminobenzamide, 711007-44-2, 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.

To a solution of 2,3-diamino-benzamide (302 mg, 2 mmol) in ether (12 mL) and DCM(9mL), methyl 2,2,2-trichloroacetimidate (0.44 mL, 2.5 mmol) and TFA (1.0 mL, 12.8 mmol)were added. The reaction mixture was stirred at room temperature for 6 h. After evaporation, andchromatography (DCM/methanol=70:1) gave the title compound 5 as a white solid (340 mg,61.3%).

Statistics shows that 2,3-Diaminobenzamide is playing an increasingly important role. we look forward to future research findings about 711007-44-2.

Reference:
Article; Zhou, Jie; Ji, Ming; Zhu, Zhixiang; Cao, Ran; Chen, Xiaoguang; Xu, Bailing; European Journal of Medicinal Chemistry; vol. 132; (2017); p. 26 – 41;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics