Month: September 2021

Synthetic Route of 87-13-8, These common heterocyclic compound, 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate, 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.

Aniline (2.733 mL, 29.99 mMol) was stirred in diethyl ethoxymethylenemalonate (6.063 mL, 30.00 mMol) at 120-130C for 16.5 hours. T.l.c. analysis (ethyl acetate cyclohexane, 1 : 1) showed the presence of one UV-active product (Rf 0.84) and complete consumption of both starting materials. Upon cooling down of the reactionsolution to room temperature, intermediate diethyl 2-((phenylamino)methylene)malonate 35 solidified (as dark yellow crystalline solid,7.899 g, quant.). M.p. 36-37C; HRMS (EIj: found 263.11531 [M] C14H17N04requires 263.11521; Vmax (thin film): 3265, 3184 (w, NH), 3050 (w, ArC-H), 2981,2936, 2904, 2871 (m, alkyl C-H), 1717 (s, 2 x intramolecularly hydrogen-bondedC=O conjugated with C=C), 1691 (s, C=C-NH), 1655 (s, C=N-), 1623 (s, aryl conjugated C=C), 1255 (s, C-N stretch) cm?; 6H (CD3CN, 500 MHz): 1.31 (3H, t, JCH3,CH2 7.1 Hz, CH3), 1.32 (3H, t, JCH3,CH2 7.2 Hz, CH3), 4.19 (2H, q, JCH2,CH3 7.2 Hz, CH2), 4.25 (2H, q, JCH2,CH3 7.1 Hz, CH2), 7.16 (1H, tt, JparaArH,metaArHs 7.4 Hz, JparaArH,orthoArHs 1.1 Hz, para-ArH), 7.20 (2H, dt, Jortho&-Hs,metaArHs 7.6 Hz,JorthoArHsparaArH 1.0 Hz, 2 x orthoArHs), 7.38 (2H, m, J 7.4 Hz, 2 x metaArHs), 8.48(1H, d, JCH,NH 13.8 Hz, CH-NH), 10.81 (1H, d, JNH,CH 13.6 Hz, CH-NI]); 6c(CD3CN, 125 MHz): 14.1, 14.2 (2 x CH3), 60.3, 60.6(2 x CH2), 93.9 (O=C-C-C=O),117.6(2 x orthoArCs), 125.1 (paraArC), 130.1 (2 x metaArCs), 139.8 (ArCquat-NH),151.9 (NH-CH), 165.6 (C=O), 168.8 (hydrogen bonded C=O).

Statistics shows that Diethyl 2-(ethoxymethylene)malonate is playing an increasingly important role. we look forward to future research findings about 87-13-8.

Reference:
Patent; UCL BUSINESS PLC; SELWOOD, David; HOBBS, Adrian; WO2015/189560; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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 69812-51-7, Formula: C8H7ClO4S

General procedure: To a solution of 23 (313 mg, 1 mmol) in DMF (1 mL), was addedtriethylamine (210 mg, 2.05 mmol), methyl 4-chlorosulfonyl benzoate27c (235 mg, 1 mmol) and 4-dimethylaminopyridine (10 mg). Themixture was stirred at rt for 4 h. The solvent was removed and the residuewas purified by a silica column with CHCl3 and MeOH to afford356 mg of 24f as a white solid in 75% yield. TLC Rf 0.13 (CHCl3/MeOH,40:1); 1H NMR (DMSO-d6) delta 1.25 (s, 9H, Piv), 2.61 (s, 3H, NCH3), 3.91(s, 3H, OCH3), 4.21 (s, 2H, NCH2), 6.28 (s, 1H, 5-H), 7.95 (d,J=8.0 Hz, 2H, Ph), 8.18 (d, J=8.0 Hz, 2H, Ph), 10.85 (s, 1H, exch,PivNH), 11.66 (s, 1H, exch, NH), 11.88 (s, 1H, exch, NH).

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:
Article; Xiang, Weiguo; Dekhne, Aamod; Doshi, Arpit; O’Connor, Carrie; Hou, Zhanjun; Matherly, Larry H.; Gangjee, Aleem; Bioorganic and Medicinal Chemistry; vol. 27; 23; (2019);,
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Related Products of 1459-93-4, 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 1459-93-4 as follows.

Methyl isophthalate (2.00 g, 11.1 mmol) was dissolved in THF (60 mL), and a 2.0 mol/L solution of dimethylamine (11.1 ml, 22.2 mmol) in methanol, EDC hydrochloride (4.27 g, 22.2 mmol) and 1-hydroxybenzotriazole monohydrate (3.40 g, 22.2 mmol) were added thereto, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate = 1:3) to afford methyl 3-(N,N-dimethylcarbamoyl)benzoate (2.30 g, 100 %).

According to the analysis of related databases, 1459-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1700856; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 49851-36-7, 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. 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

TEA (0.276 ml_, 1 .984 mmol) was added to a mixture of 3-bromobenzoic acid (199 mg, 0.992 mmol) and HATU (415 mg, 1 .091 mmol) in DMF at 23 C. In a separate vial, methyl 2-(2- aminophenyl)acetate hydrochloride (CAS 49851 -36-7) (200 mg, 0.992 mmol) was stirred with TEA (0.276 ml_, 1 .980 mmol) in DMF (0.5 ml_). After 5 min, the solution of methyl 2-(2- aminophenyl)acetate hydrochloride (200 mg, 0.992 mmol) was added to the 3-bromobenzoic acid (199 mg, 0.992 mmol) mixture and the resulting mixture was stirred at rt for 30 min. The reaction mixture was diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc. The combined organics were washed with 5% aq LiCI, dried (Na2S04) and concentrated. The resulting residue was purified by silica gel chromatography (EtOAc- heptanes 0-60%) to provide the title compound. MS (ESI+) m/z 348.0, 350.0 (M+H).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-(2-aminophenyl)acetate hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 927-68-4, 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. 927-68-4 name is 2-Bromoethyl acetate, 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.

To a solution of 2-methoxy-5-nitro-phenol (1.0 g, 5.9 MMOL) in dry DMF (20 ML), under N2, was added K2CO3 (1. 1 eq. , 0.9 g) and 2-BROMOETHYL acetate (1.1 eq, 0.714 ML). After heating to 60 C for 4 hours, a saturated solution of NH4CI was added and the mixture was extracted with DICHLOROMETHANE. The organic phase was washed with water, dried over NA2SO4, filtered and then concentrated in vacuo, to give 1.5 g of the crude intermediate compound. This was dissolved in dry methanol (34 ML) and MeONa (31 mg, 0.58 MMOL) was added. After 1H an excess of Amberlite IR120 (H+ FORM) was added, the solution was filtered and concentrated in vacuo. The residue was dissolved in DICHLOROMETHANE and washed with NAOH 0.1 N and water. The organic phase was dried over NA2SO4, filtered and then concentrated in vacuo, to give 1.1 g of the title compound as a pale yellow solid (m. p. 115 C). NMR ( H, CDCI3) : No. 7. 95 (dd, 1 H), 7.80 (d, 1H), 6.94 (d, 1H), 4.21 (t, 2H), 4.03 (t, 2H), 3.98 (s, 3H), 2.3 (bs, 1H). MS (M/Z) : 214 [MH] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromoethyl acetate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/89897; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13831-03-3, name is tert-Butyl propiolate, 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 13831-03-3, Safety of tert-Butyl propiolate

n-Butyllithium (1.6 M in hexane; 41.9 mL, 67.0 mmol) was added dropwise within 10mm at -55 to -50CC to a soln of tert-butyl propiolate (103; 8.76 mL, 63.8 mmol) in dryTHF (200 mL). The mixture was allowed to stir at -40C for 1.5 h. The mixture wascooled to -78C. A soln of 102 (7.25 g, 31 9 mmol) in THF (66 mL) was added within 10 mm with the temperature not exceeding -64C. The mixture was stirred for 0.5 h at-78C, then warmed to -40C and allowed to slowly warm to 0C over 3 h. The mixture was poured into 1 M aq. KHSO4 soln and extracted with EtOAc. The organicphase was dried (Na2SO4) and concentrated. FC (hexane/EtOAc 90:10 to 70:30) afforded the ketone 104 (8.34 g, 89%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl propiolate, and friends who are interested can also refer to it.

Reference:
Patent; POLYPHOR AG; OBRECHT, Daniel; ERMERT, Philipp; OUMOUCH, Said; PIETTRE, Arnaud; GOSALBES, Jean-Francois; THOMMEN, Marc; WO2013/139697; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 123-95-5, name is Butyl stearate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 123-95-5

An esterification reaction mixture (94 g), consisting of butanol (ca., 4.9% w/w), butyl stearate (95.1% w/w), residual stearic acid (trace), residual methanesulfonic acid catalyst (1383 ppm) and undesired butyl methanesulfonate (613 ppm) was treated with 45% aqueous KOH (229 mg, 1.84 mmol as compared to 1.74 mmol MSA originally charged to the reaction). The resulting mixture was heating at 50 C. for 40 minutes. Without wishing to be bound by any particular theory or explanation, it is believed that reaction of butyl stearate with KOH produced potassium stearate, which retains significant solubility in the butyl stearate medium. The formed potassium stearate then reacted with butyl methanesulfonate to produce potassium methanesulfonate and butyl stearate. After filtration of the by-product solid salts (0.6325 g), analysis of the mixture by gas chromatography revealed only 300 ppm unreacted butyl methanesulfonate, a 51% reduction. Repetition of the above KOH treatment at a higher temperature (175 C./60 min.) revealed complete reaction of the butyl methanesulfonate. Similarly, treatment with NaOH was found equally effective as treatment with KOH. Treatment with Ca(OH)2 proved ineffective, presumably due to formation of poorly soluble calcium salts. Treatment with acidic tin(II) or zirconium (IV) salts resulted in formation of additional butyl methanesulfonate.

According to the analysis of related databases, 123-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smith, Gary; Cordova, Robert; Chen, Johnson C.H.; Chen, Mabel; US2006/30725; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 37746-78-4, These common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, 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 the suspension of potassium phthalimide (4.5 mmol) in dry DMF (4 mL) was added a solution of (E)-alkyl -bromobut-2-enoate in dry DMF (3 mL). The reaction was run at room temperature overnight. After the reaction was omplete, the reaction mixture was poured into water and extracted with ether and concentrated in vacuum to leave a hite solid. The residue can be easily purified by flash chromatography (petroleum/ethyl acetate, 4:1), to give the desired compounds 1.

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Fuzhong; Chen, Jun; Zhang, Xiangyang; Liu, Jibing; Cun, Linfeng; Zhu, Jin; Deng, Jingen; Liao, Jian; Tetrahedron Letters; vol. 52; 7; (2011); p. 830 – 833;,
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Ester – an overview | ScienceDirect Topics

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. 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 3,4-diamino-5-bromobenzoate

In a sealed glassware, a mixture of intermediate 3a and intermediate 3b (75/25) (10 g; 28.39 mmol), N-boc-2,3-dihydro-lH-pyrrole (6.86 mL; 39.75 mmol) and K2CO3 (11.8 g; 85.18 mmol) in 1,4-dioxane (250 mL) was bubbled with N2. Then, PPh3(1.49 g; 5.68 mmol) and Pd(OAc)2(640 mg; 2.84 mmol) were added. The reaction mixture was heated to 100C for 5h. The reaction mixture was cooled down to rt, poured onto water and extracted with EtOAc. The organic layer was decanted, washed with brine, dried over MgS04, filtered and evaporated to dryness. The residue (21 g) was purified by chromatography over silica gel (irregular SiOH; 20-45 muiotaeta; 450 g; mobile phase: 62%> heptane, 3% MeOH (+10% NH4OH), 35% EtOAc). The pure fractions were collected and evaporated to dryness yielding 2.3 g (17%>, impure) of intermediate 16a and 8.2 g (59%) of intermediate 16a.

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 1245643-11-1.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; JOUSSEAUME, Thierry, Francois, Alain, Jean; (114 pag.)WO2018/178280; (2018); A1;,
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. 20637-08-5, name is Methyl 4-(4-methoxyphenyl)butanoate, A new synthetic method of this compound is introduced below., COA of Formula: C12H16O3

a) 5-(4-Methoxyphenyl)-1-(3-pyridinyl)-2-pentanone A solution of n-butyl lithium (28 ml of 1.6M in hexane, 0.124 mol) was added to a stirred solution of diisopropylamine (4.55 g, 0.045 mol) in dry tetrahydrofuran (50 ml) at 0C under a nitrogen atmosphere and the resulting yellow solution was stirred at 0C for 30 minutes. To the solution was added hexamethylphosphoramide (8.06g, 0.045 mol) and the resulting solution was stirred at 0C for 15 minutes. 3-Picoline (4.19g, 0.045 mol) was added to the reaction mixture and the resulting deep-red solution was stirred at 0C for 30 minutes. To the solution was added 4-(4-methoxyphenyl)butyric acid methyl ester (9.36g, 0.045 mol) in dry tetrahydrofuran (20 ml). The resulting mixture was stirred at 0C for 15 minutes and then at room temperature for an additional 90 minutes. The pale-yellow solution was extracted with hydrochloric acid (300 ml of 1M). The acid solution was washed with ethyl acetate (2 * 250 ml), made basic using potassium hydroxide and extracted with ethyl acetate (4 * 200 ml). The combined extracts were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield a crude product. The crude product was purified by column chromatography (silica gel, chloroform) and recrystallized from ethyl acetate-hexane to yield 5-(4-methoxyphenyl)-1-(3-pyridinyl)-2-pentanone as a colorless crystalline solid, having a melting point of 35-37C and the following physical characteristics: Elemental analysis: C,75.31%, H,7.03%, N,5.11%; as against calculated values of C,75.31%; %,7.14%, N,5.17% for C17H19NO2·0.1H2O. 1H-NMR (delta-CDCl3): 1.82-1.98 (m,2H), 2.46-2.62 (m,2H), 2.53 (t,2H), 3.67 (s,2H), 3.79 (s,3H), 6.83 and 7.06 (ABq,4H), 7.23-7.31 (m,1H), 7.29-7.37 (m,1H), 8.39-8.46 (m,1H) and 8.50-8.56 (m,1H).

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; G.D. Searle & Co.; EP267439; (1988); A3;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics