Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 13304-62-6, name is N-Benzylacrylamide, 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 13304-62-6, Formula: C10H11NO

General procedure: To a solution of compound 5 (6) (3 mmol) and substituted acrylamide (3.3 mmol) in dry DMF was added Pd(OAc)2 (3%) and triethylamine (6 mmol). The reaction mixture was stirred under 100 C via microwave (500 w) for 7 min. Then the mixture was poured into 10% HCl ice water (200 ml) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compounds 7 or 8.

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, N-Benzylacrylamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Yikai; Zhong, Hanyu; Lv, Zhiliang; Zhang, Mingfeng; Zhang, Tao; Li, Qisheng; Li, Ke; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 158 – 167;,
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Synthetic Route of 67442-07-3, These common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, 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.

C. Synthesis of Intermediate 22 [0244] A 3-neck flask was charged with 21 (100 g) and THF (800 mL). The solution was degassed three times by slowly applying vacuum, followed by breaking vacuum with nitrogen. The solution was cooled to -10 C. internal temperature. A solution of 2N i-PrMgCl solution in THF (125 g, 1.04 mole equiv) was added slowly while maintaining internal temperature at -10 C. to 0 C. The resulting mixture was then stirred for 30 minutes at -10 C. until reaction was complete. 2-Chloro-N-methoxy-N-methylacetamide (40.6 g, 1.20 mole equiv) was dissolved in MTBE (122 g, 1.22 wt equiv) and filtered through a 1 mum filter. The MTBE solution of the acetamide was then added slowly to the flask maintaining internal temperature at -10 C. to 0 C. Upon completion of the addition, the internal temperature was adjusted to 0 C. and agitated for 2 hours. After the reaction is complete, 1N HCl (750 g) was added slowly so that the internal temperature did not exceed 20 C. If necessary, the internal temperature was adjusted to 20 C. The layers were separated and the aqueous layer was extracted with MTBE (410 g). The organic layers were combined and dried over MgSO4. The MgSO4 was filtered off and rinsed with THF (200 g). The filtrate and rinse were concentrated under vacuum 10 volumes (1000 mL). Isopropanol (785 g) was added and small amounts of crystals began to form. This slurry was again concentrated under vacuum to 10 volumes (1000 mL). Isopropanol (785 g) was once again added and the slurry was concentrated under vacuum to 10 volumes (1000 mL). The internal temperature was adjusted to 20-25 C. and agitated for ca. 30 minutes. The slurry was filtered and rinsed with isopropanol (100 g) then dried under vacuum to provide 62.28 g (70.8%, 98% purity by HPLC) of the product 22 as an off-white to pale yellow solid. 1H NMR (400 MHz, CDCl3, delta): 8.19 (s, 1H), 8.12 (d, J=7.8 Hz, 1H), 7.82 (s, 1H), 7.67 (d, J=8.0 Hz, 2H), 7.52 (d, J=7.8 Hz, 1H), 4.71 (s, 2H). 19F NMR (376 MHz, CDCl3) delta -111.4 (s, 2F).

Statistics shows that 2-Chloro-N-methoxy-N-methylacetamide is playing an increasingly important role. we look forward to future research findings about 67442-07-3.

Reference:
Patent; Scott, Robert William; Wang, Fang; Shi, Bing; Mogalian, Erik; US2013/324496; (2013); A1;,
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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. 116861-31-5, name is tert-Butyl (3-chloropropyl)carbamate, A new synthetic method of this compound is introduced below., COA of Formula: C8H16ClNO2

To a refluxing solution of hydrazine hydrate (6.40 g, 128.00 mmol) in ethanol (14.5 mL) was added a solution of tert-butyl 3-chloropropylcarbamate (9A) (3.80 g, 19.62 mmol) in ethanol (14.5 mL), dropwise over 80 min. The mixture stirred at reflux for 1 h. The reaction mixture was then evaporated and the residue diluted with diethyl ether (60 mL). The two layers were separated. The organic layer was washed with saturated sodium carbonate solution (17 mL) and evaporated to give tert-butyl 3-hydrazinylpropylcarbamate (10A) (1.60 g, 8.45 mmol, 43%) as a yellow oil. The crude material was used in the next step without further purification. ESMS m/z 190 (M+H)+.

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; SOVA PHARMACEUTICALS, INC.; STEIN, Gregory; RAO, Srinivas, G.; DURON, Sergio, G.; CHAPMAN, Justin; SYDSERFF, Simon, G.; WO2014/18571; (2014); A2;,
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Adding a certain compound to certain chemical reactions, such as: 148017-28-1, name is tert-Butyl sulfamoylcarbamate, 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 148017-28-1, Safety of tert-Butyl sulfamoylcarbamate

Example 65; N-[((1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-hydroxycyclopentyl)methyl]sulfamide (Compound I-56); Step a: tert-butyl(aminosulfonyl)[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl]carbamate; ((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methanol (700.0 mg, 0.001462 mol), N-Boc-sulfonamide (398 mg, 0.00203 mol) and triphenylphosphine (575 mg, 0.00219 mol) were dissolved in ethyl acetate (28 mL, 0.28 mol) at 50 C. under an atmosphere of nitrogen. Diethyl azodicarboxylate (350.0 muL, 0.002223 mol) was added over 2-3min and the mixture was stirred at 50 C. for 30 minutes. The cooled mixture was evaporated and the residue purified by silica gel chromatography, eluting with 10 to 100% ethyl acetate in hexanes, to yield the product as a white solid, 636 mg (66%). LC/MS: Rt=2.55 min, ES+ 657 (AA standard).

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; Millennium Pharmaceuticals, Inc.; US2007/191293; (2007); A1;,
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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. 255735-88-7, name is tert-Butyl 2-aminopropylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of tert-Butyl 2-aminopropylcarbamate

To a solution of tert-butyl 2-aminopropylcarbamate (3.6 g, 20.6 mmol), 2-hydroxybenzoic acid (2.79 g, 20.6 mmol) and imidazole (1.41 g, 20.6 mmol) in EtOAc (100 mL) at 0° C. was slowly added a solution of DCC (4.26 g, 20.6 mmol) in EtOAc (50 mL). The reaction mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography, EtOAc/Petroleum ether (0-20percent) to afford tert-butyl 2-(2-hydroxybenzamido)propylcarbamate (2.4 g, 40percent) as a white solid.

The synthetic route of 255735-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Smith, Jesse J.; US2010/41748; (2010); A1;,
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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. 37045-73-1, name is 3-(Methylsulfonamido)aniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H10N2O2S

In a 1000 mL four-necked flask with mechanical stirring and a thermometer,Add 700g of water,Methanesulfonamidoaniline 149g(content 80%, 0.64 mol), sodium carbonate 140 g (1.32 mol),Stir well and then as solution A,Transfered to the pipeline reactor by screw pump A,At the same time pumping liquid 1-chloropropane 143g (1.82mol),Solution A and 1-chloropropane are fed with screw pump A and screw pump B, respectively.The mass flow rate ratio of the control solution A to 1-chloropropane was 6.9:1.0.The pipeline reactor has a pipeline reaction section providing a chemical reaction site, and the solution A and 1-chloropropane are continuously reacted in the pipeline reaction section.Keep the temperature of the pipeline reaction section at 100 C,Control the residence time of the reaction solution for 30 min, cooling,Extracted with 800 mL of anisole,The combined organic phases are concentrated under reduced pressure.Obtaining dialkylaminomethanesulfonanilide157.6g,97.9%,The yield was 91.2%.

According to the analysis of related databases, 37045-73-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JIANGSU DIAN CHEMICAL CO LTD; Jiangsu Di’an Chemical Co., Ltd.; ZHEJIANG SHANYU TECH CO LTD; Zhejiang Shanyu Technology Co., Ltd.; TAO ANNI; Tao Anni; GUO HAIBIN; Guo Haibin; WEI BIN; Wei Bin; LI JIAN; Li Jian; ZHENG TUCAI; Zheng Tucai; XU XUMING; Xu Xuming; HU XIAOKUI; Hu Xiaokui; (6 pag.)CN108299250; (2018); A;,
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Some common heterocyclic compound, 78191-00-1, name is N-Methoxy-N-methylacetamide, molecular formula is C4H9NO2, 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. HPLC of Formula: C4H9NO2

A suspension of 6-bromo-3-isopropyl[1 ,2,4]triazolo[4,3-a]pyridine hydrochloride (1.00 g, 3.62 mmoi) in THF (18.0 mL) was charged with a positive stream of nitrogen and cooled to 0 0C. The resulting suspension was then treated with commercially available solution of isopropylmagnesium chloride in diethyl ether (2.0 M THF solution, 3.5 mL, 7.0 mmol). The internal temperature of the reaction was not allowed to exceed 0 0C. The resulting dark solution was allowed to stir for 1 hour and then the reaction was treated with N-methoxy-N-methyl acetamide. After 4 hours, the reaction was quenched with 100 mL of saturated ammonium chloride solution and was extracted with ethyl acetate (3 X 250 mL). The resulting organic extract was Na2SO4 dried, filtered, and concentrated in vacuo to a residue that was directly subjected to normal phase silica chromatography (60 % ethyl acetate, 30 % hexanes, 10 % MeOH) to furnish a gum (743 mg, 85 %). 1H NMR (300 MHz, O4-MeOH) delta 9.02 (s, 1 H), 7.87 (dd, J= 9.7, 1.5 Hz, 1 H), 7.68 (dd, J= 9.6, 1.1 Hz, 1 H), 3.72 (septet, J = 6.8 Hz, 1 H), 2.68 (s, 3H), 1.51 (d, J= 6.8 Hz1 6H); LC/MS C-18 column, tr = 0.48 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min with detection 254 nm, at 50 0C). ES-MS m/z 204 (M+H). ES-HRMS m/z 204.1158 (M+H calcd for C11H14N3O requires 204.1131).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 78191-00-1, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/18735; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 17641-08-6, 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. 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To the appropriate Schiff bases of isatin (10 mmol) in8-10 cm3 of anhydrous DMF, K2CO3 (15 mmol) was addedand stirred at room temperature for 1 h. After completion of1 h, the solution turned red brown in color. Appropriatechloroanilides (10 mmol) and KI (2 mmol) were then addedto this solution drop wise and heated at 60 C for 5.5-9 h.After conforming the end of reaction by TLC (ethyl acetate:n-hexane 30:70), the mixture was poured into ice cold water.Precipitated crude product was filtered and washed thoroughlywith cold water (3 9 200 cm3). Compounds wererecrystallized from ethanol/water mixture (1:1). Reactiontimes, melting points, and yields are depicted in Table 1.

The synthetic route of 2-Chloro-N-(3-methoxyphenyl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Debnath, Biplab; Ganguly, Swastika; Monatshefte fur Chemie; vol. 147; 3; (2016); p. 565 – 574;,
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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 98-64-6 as follows. Application In Synthesis of 4-Chlorobenzenesulfonamide

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 (10percent), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 .x. 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, 98-64-6, 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;,
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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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H8ClNO2

To a 10L four necked flask was charged l-Isopropyl-3-methyl-lH-l,2,4-triazole 7 (400 g) in THF (2.5 L). The resulting solution was cooled to -40 C and 2.5 M n-butyllithium BuLi in n- hexanes (1.41 L) was added while keeping the internal temp, below -20C. The resulting yellow suspension was stirred at -40C for 1 hour before being transferred. To a 20L flask was charged 2-chloro-N-methoxy-N-methylacetamide 10 (485 g) in THF (4 L). The resulting solution was cooled to -40 C at which point a white suspension was obtained, and to this was added the solution of lithiated triazole 7 keeping the internal temp, below -20C. At this point a yellow orange solution was obtained which was stirred at – 30C for lhour. Propionic acid (520 mL) was added keeping the internal temp, below -20C. The resulting off-white to yellowish suspension was warmed to -5 C over 30 minutes. Citric acid (200 g) in water (0.8 L) was added and after stirring for 5 minutes a clear biphasic mixture was obtained. At this point stirring was stopped and the bottom aqueous layer was removed. The organic phase was washed with 20w% K3PO4 solution (1 L), 20w% K2HP04 solution (2 L), and 20w% NaCl solution (1 L). The organics was reduced to ca 4L via distillation under vacuum to afford 2-chloro-l-(l-isopropyl-3- methyl-lH-l,2,4-triazol-5-yl)ethanone 13 as a dark amber liquid which was used “as is” in the next step.

According to the analysis of related databases, 67442-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ANGELAUD, Remy; BEAUDRY, Danial; CARRERA, Diane; MALHOTRA, Sushant; REMARCHUK, Travis; ST-JEAN, Fredric; WO2014/140073; (2014); A1;,
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