Tag: M.W=100-200

1128-76-3, 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. 1128-76-3, name is Ethyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The following experimental procedure for the synthesis of morpholino(phenyl)-methanone is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.18 mL, 2.1 mmol) and 10 mL THF. After cooling to 0 C, DIBALH (2.0 mL, 1.0 M in hexane, 2.0 mmol) was added dropwise and stirred for 3 h at same temperature. To a reaction mixture was slowly added ethyl benzoate (0.14 g, 1.0 mmol) and stirred for 10 min. The reaction was stopped by the aqueous 1 N HCl (10 mL) and extracted with diethyl ether (2*10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel yielded morpholino(phenyl)methanone (184 mg, 96%).

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

Reference:
Article; Jeon, Ah Ram; Kim, Min Eai; Park, Jae Kyo; Shin, Won Kyu; An, Duk Keun; Tetrahedron; vol. 70; 29; (2014); p. 4420 – 4424;,
Ester – Wikipedia,
Ester – 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. 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, A new synthetic method of this compound is introduced below., 61367-07-5

Example 19(1r,4R)-4-(2-phenyl-1H-indole-6-sulfonamido)-N-((R)-1-(pyridin-2-yl)ethyl)cyclohexanecarboxamide Step 1. Preparation of (1r,4r)-methyl 4-(4-chloro-3-nitrophenylsulfonamido)cyclo hexanecarboxylate; (1r,4r)-methyl 4-aminocyclohexanecarboxylate HCl salt (7.75 g, 40 mmol) was suspended in a mixture of DCM (50 mL) and then treated with triethylamine (22.31 mL, 160 mmol), followed by 4-chloro-3-nitrobenzene-1-sulfonyl chloride (11.27 g, 44 mmol). The reaction mixture was stirred at rt for 2 h and then concentrated under reduced pressure. The residue was taken up in ethyl acetate (100 mL) and washed with 1N aq. HCl (3¡Á100 mL), brine (100 mL) and dried over sodium sulfate. Filtration and concentration of the organic solution gave product (14.1 g) as a yellow solid (MS: (M+H)+=377.3).

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; NOVARTIS AG; US2012/28969; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

35180-01-9, Adding some certain compound to certain chemical reactions, such as: 35180-01-9, name is Chloromethyl isopropyl carbonate, 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 35180-01-9.

To a solution of anhydrous sodium iodide (6 g, 40 mmol ) in anhy. acetonitrile (20 mL) chloromethyl isopropyl carbonate (2.9 g, 19 mmol) in anhyd. acetonitrile (10 mL) was added dropwise over 20 min. The reaction mixture, covered with aluminum foil (protected from light) was stirred at room temperature overnight. The solid separated was filtered, washed with acetonitrile and the filtrate was concentrated under reduced pressure. Residue was dissolved in water (10 mL) and organics were extracted in ether (25 mL). Ether extracts were washed with sodium bisulfite (5%, 10 mL), later brine (10 mL). Organic layer was dried over anhd. sodium sulfate, filtered, concentrated and dried under high dried vacuum. Yield 2.72 g (58%); 1H-NMR delta 1.3 (d, 6H), 4.95 (m, 1H), 5.95 (s, 2H).

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 35180-01-9.

Reference:
Patent; Iyer, Radhakrishnan P.; Padmanabhan, Seetharamaiyer; US2007/149462; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 4341-76-8, name is Ethyl 2-butynoate, 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 4341-76-8. 4341-76-8

General procedure: To a solution of 2-aminoaryl carbonyl 1 (0.5 mmol), MCM-41-PPh3-AuCl (128 mg, 0.05 mmol), AgOTf (12.9 mg, 0.05 mmol) in DMF (5 mL) was added internal alkyne 2 (0.75 mmol) under Ar. The reaction mixture was stirred at 100C for 4 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (20 mL) and filtered. The gold catalyst was washed with NH3¡¤H2O (2 ¡Á 5 mL), distilled water (5 mL), and acetone (2 ¡Á 5 mL) and reused in the next run. The filtrate was washed with water (2 ¡Á 10 mL) and brine (2 ¡Á 10 mL), and the organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 15/1) to afford the desired product 3.

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 Ethyl 2-butynoate.

Reference:
Article; Hu, Wenli; Yang, Weisen; Yan, Tao; Cai, Mingzhong; Synthetic Communications; vol. 49; 6; (2019); p. 799 – 813;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 140-39-6, name is p-Tolyl Acetate, molecular formula is C9H10O2, 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. 140-39-6.

NBS (13.91 g, 0.12 mol, 0.9 eq) and AIBN (2.17 g, 0.01 mol,0.1 eq) were placed in a Schlenk flask and put under an argonatmosphere. CHCI3was added followed by p-toy acetate (19.67 g, 0.13 mol). The mixture was refluxed for 4 h. After cooling down the volume of the mixture was reduced on rotavap to approximately a third and the suspension was filtered. 200 mL of CHCI3was added to the filtrate and it was 3x washed with 80 mL of water, the combined organic layers were dried with MgSC>4, filtered and volatiles were removed on rotavap. 5 mL of AcOEt was added, the mixture was shortly sonicated and while stirring, 40 mL of hexane was added causing precipitation. The mixture was put to a freezer overnight and then filtered washing the white solid with 25 mL of hexane giving 12.05 g (41 %, 0.05 mol) of the product. It was stored in the freezer. The NMR spectrum was in accordance with the literature (J. Org. Chem. 1981, 46 (15), 3029-3035)

The synthetic route of p-Tolyl Acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE JOHNS HOPKINS UNIVERSITY; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY AS CR V.V.I.; SLUSHER, Barbara; RAIS, Rana; VAVRA, Jan; TICHY, Toma?; MAJER, Pavel; JANCARIK, Andrej; TENORA, Luka?; (148 pag.)WO2018/94334; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

40800-65-5, A common compound: 40800-65-5, name is Ethyl 4-amino-3-methylbenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of ethyl 4-amino-3-methylbenzoate (7.43 g)in DMF ..(35 ml) were added DMAP (506 mg) and acetic anhydride(4.66 g) at ambient temperature. After stirring for 4 hours,the reaction mixture was diluted with water (40 ml) andextracted with EtOAc (4 x 60 ml). The combined organicextracts were washed with saturated NaHCOs (2 x 30 ml) andbrine (3 x 100 ml) . The organic layer was dried over MgSC>4 andfiltered. Evaporation gave a residue which was triturated withEtOAc – n-hexane to give ethyl 4-(acetylamino)-3-methylbenzoate(4.324 g) as white crystals. The filtrate was evaporated andtriturated with EtOAc – n-hexane to give second crop (1.64 g).NMR(DMSO-d6,8) :. 1.31 (3H, t, J = 7.1Hz), 2.11 (3H, s) , 2.28(3H, s), 4.29 (2H, q, J = 7.1 Hz), 7.7-7.8 (3H, m), 9.37 (1H,br s) .MS: 244 (M+Na). .

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, Ethyl 4-amino-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAICEL CHEMICAL INDUSTRIES, LTD.; WO2004/108686; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, belongs to esters-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 25597-16-4, 25597-16-4

The resulting product (0.50, 2.6mmol) from step 5, ethyl 4,4,4-trifluorocrotonate (1.7g, 10.1mmol) and anhydrous potassium carbonate (0.36g, 5.6mmol) were dissolved in DMF (20mL), and then the system was stirred for 2hrs at 90C. At the end of reaction, the reaction system was cooled to room temperature and added with water, the mixture was extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 0.50g of the product (50%) by column chromatography. 1HNMR (400 MHz, d-CDCl3), delta 7.65(s, 1H), 7.16 (s, 1H), 7.07(s, 1H), 5.73(m, 1H), 4.30(m, 2H),1.27(m,3H)

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, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Institute Of Biomedicine And Health, Chinese Academy Of Sciences; ZHANG, Yanmei; TALLEY, John Jeffrey; OBUKOWICZ, Mark G.; TU, Zhengchao; TORTORELLA, Micky; WANG, Yican; LIU, Jianqi; CHEN, Yan; LIU, Xiaorong; LU, Xin; EP2845854; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 18595-18-1

Example 1 A Preparation of 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(dimethylcarbamoyl)-1H- indazol-3-yl)cyclohex-3-enecarboxylic acid (1A) Step 1: Preparation of methyl 1H-indazole-6-carboxylate (A-2). Methyl 3-amino-4-methylbenzoate (A-l) (5.0 g, 30.2 mmol) was dissolved in AcOH (140 mL). Sodium nitrite (2.1 g, 30.2 mmol) in water (3.5 mL) was added drop-wise to the solution of starting material under ice-cooling at room temperature. The ice bath was removed and the mixture was stirred overnight. The half of the solvents were evaporated, the mixture was diluted with water (80 mL) and extracted with EtOAc(3×30 mL). The collected organic phase was washed with water and brine (2×200 mL), dried and evaporated to afford 2 (4.4 g), yield 83%. LCMS (ESI): calc’d for C9H8N202, [M+H]+: 177, found: 177.

The synthetic route of 18595-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; WO2014/26328; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

13831-03-3, 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. 13831-03-3, name is tert-Butyl propiolate, This compound has unique chemical properties. The synthetic route is as follows.

To ethyl cyanoformate (10 g, 101.01 mmol) was added NH2OH-HCl (8.4 g, 121.74 mmol), K2CO3 (19.9 g, 144.20 mmol), and CH2C12/H2O (100 mL). The resulting mixture was stirred for 12 hr at room temperature. The solids were filtered out and the filtrated was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 6 g (45%) of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate as a white solid. To a mixture of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate (1 g, 7.58 mmol) and tert-butyl propiolate (940 mg, 7.46 mmol) was added Et3N (765 mg, 7.57 mmol) and toluene (50 mL). The resulting solution was stirred at 140 0C for 1 min. The resulting mixture was washed with 50 mL of H2O and then was extracted with 3 x 50 mL of dichloromethane. The organic layers were combined and washed with 20 mL of brine, then dried over anhydrous sodium sulfate. Evaporated the solvents and the residue was purified onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 1.1 g (61%) of 5 -tert-butyl 2-ethyl lH-imidazole-2, 5-dicarboxylate as a yellow solid.

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; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 106614-28-2, name is Methyl 2,4-difluorobenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 106614-28-2

To a three-necked flask was added 100 g of 5-hydroxy-7-azaindole (746 mmol), 141 g of methyl 2,4-difluorobenzoate(821 mmol), 237 g of potassium phosphate (1.12 mol) and 500 mL of diethylene glycol dimethyl Ether, 110 C for 24 h (HPLC to monitor 5-hydroxy-7-azaindole).The reaction solution was concentrated to dryness, and 2L of ethyl acetate and 2 L of water were added. The organic phase was separated,dried over anhydrous sodium sulfate, and concentrated to dry crude.The crude product was heated to reflux with 1260 mL of ethyl acetate. The mixture was slowly added dropwise to a solution of 1260 mL ofpetroleum ether. After 1 h of dropping, the mixture was stirred for 1 h, slowly cooled to 25 C, filtered and dried to give163g of pale white solidRate of 76.5%.HPLC purity 98%.

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, 106614-28-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hangzhou Keyao Pharmaceutical Technology Co., Ltd.; Zhou Junming; (10 pag.)CN107089981; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics