Tag: M.W=100-200

Reference of 105-53-3,Some common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, 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.

Under the protection of nitrogen, the 100g c diethyl malonate, 300 ml anhydrous ethanol into 1000 ml three port in round bottomed flask, under room temperature, adding 40.5g sodium methoxide, then, slowly adding 102.8g bromo n-butane, after adding heating reflux, the reaction 3h; to cool down to room temperature, then adding 40.5g sodium methoxide, then, slowly adding 102.8g bromo-butane, heating reflux reaction 3h. Cooling to room temperature, removing the solvent, by adding 1 mol/L sulfuric acid aqueous solution in the pH value and system to 7 the left and the right, washing the organic phase, is distilled under reduced pressure to obtain the dibutyl c diethyl malonate, 154g (yield 90.6%).

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

Reference:
Patent; Chinese Academy Of Sciences Shanghai Advanced Institute; Jiang Yang; Li Jiusheng; Xu Jian; (6 pag.)CN106748724; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 426-65-3, name is Ethyl Pentafluoropropionate, 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 426-65-3, Computed Properties of C5H5F5O2

Compound 14 (1.2 g, 3.7 mmol) was dissolved in dry toluene (40 mL). Sodium hydride (0.18 g, 40% dispersion in oil) was added, and the mixture was stirred for 15 min at rt. Ethyl pentafluoropropionate (1.1 niL, 7.4 mmol) was added, and the mixture was stirred overnight at rt. Hydrochloric acid (IM, 40 mL) and dichloromethane were added, and the mixure was stirred for 10 min.The organic phase was separated, and the aqueus phase was extracted twice with dichloromethane. The combined organic phases were dried and concentrated. . Purification on silica gel (eluent 10% MeOH in CH2Cl2, v/v) yielded the title compound. 1H NMR (CDCl3): ? 7.71 (2H, d, J 7.9); 7.36 (IH, d, J 3.8); 7.30 (2H, d, J 7.9); 6.73 (IH, d, J 3.4); 6.06 (IH, s); 4.21 (2H, t, / 6.5); 3.12 (2H, m); 2.42 (3H, s).

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Reference:
Patent; WALLAC OY; WO2009/115644; (2009); A1;,
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Reference of 10601-80-6, 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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step-a Synthesis of 3,3-diethoxypropanoic acid To a stirred suspension of ethyl 3,3-diethoxypropanoate (15.0 g, 78.88 mmol) in water (32 mL) was added NaOH (4.10 g, 102.6 mmol) and heated to 110 C. for 1.5 h. After completion of the reaction, the reaction mixture was cooled, acidified to pH?3 with aq. 3N HCl and extracted with EtOAc (500 mL*2). The organic layer was washed with water (200 mL), brine (100 mL), dried over sodium sulphate and concentrated. The residue was used for next step without further purification (11.50 g, 91%). 1H NMR (400 MHz, DMSO-d6): delta 12.20 (s, 1H), 4.81 (t, J=5.9 Hz, 1H), 3.58-3.59 (m, 2H), 3.48-3.40 (m, 2H), 2.60-2.40 (m, 2H), 1.09 (t, J=7.3 Hz, 6H).

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

Reference:
Patent; Orion Corporation; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; SASMAL, Sanjita; HOSAHALLI, Subramanya; (77 pag.)US2016/368906; (2016); 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. 18358-63-9, name is Methyl 4-(methylamino)benzoate, A new synthetic method of this compound is introduced below., SDS of cas: 18358-63-9

For example, some of the silylamines used in the examples below were prepared as follows from the free amine. (i) TMSCI, NEt3, CH2CI2, 17h (ii) a. n-BuLi, THF,-78C, 2 h. b. TMSCL, rt, 17h The silylamines where RN2 is sulfonyl were prepared as follows from a modified amine by heating with bis (trimethylsilyl) trifluoroacetamide (BSTFA). 0 R’ +, 1 MeCN, reflux RW NHTs + I R F CO 3 h, 95%-si- ti – SI- The silylamines were purified by vacuum distillation. Once purified, their were handled under nitrogen at all times, and stored at-20C

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; CAMBRIDGE UNIVERSITY TECHNICAL SERVICES LIMITED; ASTRAZENECA UK LIMITED; WO2005/90283; (2005); 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. 35180-01-9, name is Chloromethyl isopropyl carbonate, A new synthetic method of this compound is introduced below., Formula: C5H9ClO3

Preparation of Compound 167Compound 167. A 20 mL microwave vial was charged with starting acid (300 mg, 0.651 mmol), potassium carbonate (117 mg, 0.847 mmol), sodium iodide (68.3 mg, 18.6 mu, 0.456 mmol), DMF (10 mL) and chloromethyl isopropyl carbonate (119 mg, 0.782 mmol). Heated at 80 C in microwave for 20 min, then the reaction mixture was partitioned between EtOAc and water (80 mL each). The organic layer was separated, washed with water then brine (80 mL each), dried (magnesium sulfate), filtered and concentrated. The resulting residue was purified by MPLC using an Isco Combiflash (40 g column) 0-80% EtOAc in hexanes linear gradient over 24 column volumes at 40 mL/min. Product isolated from column was dissolved in MeCN (10 mL), treated with water (8 mL) then the resulting mixture was frozen and lyophilized. Gave 167 (306 mg, 0.519 mmol, 80%) as a white solid. Analysis carried out by LCMS (60-98% aqueous MeCN, formic acid modifier, 7 min, C4) ESI-MS m/z calc. 576.2869, found 577.57 (M+l)+; Retention time: 3.05 minutes. (1H NMR shows rotamers) 1H NMR (300.0 MHz, DMSO) delta 7.33 (s, 0.55H), 7.24 (s, 0.45H), 5.89 (d, J = 6.3 Hz, 0.55H), 5.81 (dd, J = 6.3, 8.0 Hz, 1H), 5.73 (d, J = 6.3 Hz, 0.45H), 5.58 (t, J = 7.5 Hz, 0.45H), 5.16 (d, J = 2.4 Hz, 0.55H), 4.87 – 4.85 (m, 1H), 3.11 (s, 1.65H), 3.02 (s, 1.35H), 2.85 (s, 1.65H), 2.63 (s, 1.35H), 1.99 – 1.86 (m, 1H), 1.67 – 1.35 (m, 6H), 1.34 – 1.08 (m, 18H) and 0.82 – 0.51 (m, 8H) ppm.

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; VERTEX PHARMACEUTICALS INCORPORATED; GREEN, Jeremy; WILSON, Dean, M.; KONG, Laval, Chan Chun; DAS, Sanjoy, Kumar; POISSON, Carl; COURT, John, J.; TANG, Qing; LI, Pan; COLLIER, Philip, N.; WAAL, Nathan; LAUFFER, David, J.; DORSCH, Warren; WO2012/6055; (2012); A2;,
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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. 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl (E)-3-Ethoxyacrylate

To a reactor was charged K3PO4 (4104 g granular, 19.3 moles), ethyl 3-amino-lH-pyrazole-4-carboxylate (2000 g, 12.9 moles), and DMF (18.8 kg) and the mixture was agitated. After 20 min, (?)-ethyl 3- ethoxyacrylate, (2230 g, 15.5 moles) was added and the mixture was heated to 110-115 C internal temperature (IT). After the reaction was judged to be complete based on consumption of starting material , heating was ceased. The mixture was allowed to stir and cool overnight. Aqueous hydrochloric acid (3 M, 13 L) was added over ~ 2 h. DI water (6 L) was added and the mixture was allowed to stir overnight. The mixture was filtered through polypropylene filter cloth (PPFC) and the residue was washed with water (3 x 5 vol, 3 x 10 L). The solid was placed in trays and oven dried under vacuum at 55 C for 3 days and then 45 C for 4 days to constant weight of (2553 g 95.6%).

The synthetic route of 5941-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHAO, Qian; SPENCER, Stacey; JIANG, Yutong; HAAS, Julia; EARY, Charles Todd; (335 pag.)WO2018/81417; (2018); A2;,
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Synthetic Route of 50893-36-2, These common heterocyclic compound, 50893-36-2, name is 1-Chloroethyl ethyl carbonate, 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 solution of 2-(3-{6-[2-(2,4-dicUoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2- methyl-propionic acid [100 mg, 0.218 mmol, Example 49(b)] in dimethylformamide (2 mL) is added 1-chloroethyl ethyl carbonate (0.053 mL, 0.392 mmol) and Cs2CO3 (142 mg, 0.436 mmol). The mixture is heated under microwave at 11O0C for 10 minutes, quenched with water, and extracted with ethyl acetate. Combined organic layers are washed with brine, dried over sodium sulfate and concentrated. The residue is subjected to silica gel chromatography eluting with 0 to 40percent EtOAc in heptane to obtain 2-(3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2- methyl-propionic acid 1 -ethoxycarbonyloxy-ethyl ester as an oil which is treated with IM hydrogen chloride in ether affording 2-(3-{6-[2-(2lambda-dicMoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl|- phenyl)-2-methyl-propionic acid 1-ethoxycarbonyloxy-ethyl ester hydrochloride [80 mg, 64percent, Example 50] as a solid. LC/MS: R7 = 2.94 minutes, MS: 576 (M+H). 1H NMR [300 MHz, (CD3)2SO]: delta 7.36 – 7.8 (7H, m), 6.64 (IH, q), 6.6 (IH, s), 4.05 (2H, q), 3.96 (3H, s), 3.68 (2H, m), 3 (2H, m); 1.57 (6H, s), 1.38 (3H, d), 1.15 (3H, t). IC50 = 4 nM

Statistics shows that 1-Chloroethyl ethyl carbonate is playing an increasingly important role. we look forward to future research findings about 50893-36-2.

Reference:
Patent; SANOFI-AVENTIS U.S. LLC; HARRIS, Keith John; WO2008/39882; (2008); A1;,
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Electric Literature of 87-24-1,Some common heterocyclic compound, 87-24-1, name is Ethyl 2-methylbenzoate, molecular formula is C10H12O2, 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.

Ethyl 2-methylbenzoate (2.0 g, 12.2 mmol) was dissolved in 30 ml carbon tetrachloride. N-bromosuccinimide (2.17 g, 12.2 mmol) and benzoyl peroxide (80 mg, 0.33 mmol) were added and the mixture was heated at 80?C for 4 h. The mixture was allowed to cool and was stirred at room temperature overnight. The mixture was filtered and the solvent was evaporated to give 3.0 g (11.8 mmol, 97%) of the title compound as a yellow oil. Purity 96%. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.43 (t, J=7.23 Hz, 3 H), 4.42 (q, J=7.29 Hz, 2 H), 4.96 (s, 2 H), 7.38 (t, J=7.42 Hz, 1 H), 7.44 – 7.55 (m, 2 H), 7.97 (d, J=7.82 Hz, 1 H). HPLC/MS (9 min) retention time 6.30 min. LRMS: m/z 243 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-methylbenzoate, its application will become more common.

Reference:
Patent; Almirall, S.A.; EP2457900; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

140-39-6, name is p-Tolyl Acetate, belongs to esters-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. Formula: C9H10O2

p-Tolyl acetate 2b (10 gm, 0.067 mol) was in 500 mL round bottom flask containing aluminium chloride (10.7 gm, 0.08 mol). It was heated on an oil bath at 140-150 C for 5-6 hr. The progress of the reaction was monitored by TLC using ethyl acetate:hexane as a solvent system. The reaction mixture was quenched with crushed ice and obtained solid product was extracted with ethyl acetate (2¡Á50 mL). The organic extracts were washed with brine solution (2¡Á15 mL) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to afford the corresponding crude compounds. The obtained compound 3b was recrystallized using aq. ethanol. Yield 92%. M.p. 45-48 C.

The synthetic route of 140-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shaikh, Mubarak H.; Subhedar, Dnyaneshwar D.; Khedkar, Vijay M.; Jha, Prakash C.; Khan, Firoz A. Kalam; Sangshetti, Jaiprakash N.; Shingate, Bapurao B.; Chinese Chemical Letters; vol. 27; 7; (2016); p. 1058 – 1063;,
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Some common heterocyclic compound, 37466-90-3, name is Ethyl 3,4-diaminobenzoate, molecular formula is C9H12N2O2, 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: C9H12N2O2

General procedure: The mixture of ethyl 3,4-diaminobenzoate 19 (1 eq., 13.6 mmol), appropriate carboxyaldehyde (1,5 eq., 20.4 mmol) and p-toluenesulphonic acid (0,2 eq., 2.72 mmol) in toluene (150 mL) was heated at reflux with Dean-Stark apparatus for 6 h. After completion of the reaction (TLC control) the whole was concentrated and chromatographed on silica gel (heptane/ethyl acetate, gradient 0-60 % or CHCl3/MeOH 0-5 %). 4.1.14.1 Ethyl 2-(1,3-thiazol-2-yl)-1H-1,3-benzodiazole-6-carboxylate (20h) Synthesized from 19 (5,0 g, 27,7 mmol, 1 eq.) and 2-thiazolecarboxaldehyde (3,56 g, 30,5 mmol, 1,1 eq.). Solid, 7,4 g (yield 88 %). 1H NMR (300 MHz, CDCl3): delta 8.88 (d, J = 0.9 Hz, 1H), 8.01 (d, J = 3.2 Hz, 1H), 7.91 (d, J = 1.8 Hz, 1H), 7.83 (dd, J = 8.4, 1.9 Hz, 1H), 7.50 (dd, J = 3.2, 1.0 Hz, 1H), 6.75 (d, J = 8.4 Hz, 1H), 4.75 (s, 2H), 4.34 (q, J = 7.1 Hz, 2H), 1.39 (dd, J = 8.7, 5.6 Hz, 3H). API-ES: m/z 272.1 [M-H]-

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 37466-90-3, its application will become more common.

Reference:
Article; Moszczy?ski-P?tkowski, Rafa?; Majer, Jakub; Borkowska, Ma?gorzata; Bojarski, ?ukasz; Janowska, Sylwia; Mat?oka, Miko?aj; Stefaniak, Filip; Smuga, Damian; Bazyd?o, Katarzyna; Dubiel, Krzysztof; Wieczorek, Maciej; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 96 – 116;,
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