Month: June 2021

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;,
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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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H16O3

To a solution of ethyl 4-hydroxycyclohexanecarboxylate 2 (mixture of cis and trans) (2.5 g, 14.5 mmol) and imidazole (1.97 g, 29 mmol) in anhydrous DMF (20 mL), tert-butyldimethylsilyl chloride (2.63 g, 17.5 mmol) was added. After stirring overnight, Et2O (60 mL) and 1M aqueous HCl (60 mL) were added. After extraction with Et2O, the combined organic phases were washed with 1M aqueous HCl and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give a TBS-protected alcohol as a colorless oil (4.14 g), which was used in the next step without further purification. To a solution of the former alcohol (4.14 g, 14.5 mmol) in THF (20 mL) and methanol (12 mL), lithium hydroxide (0.7 g, 29 mmol) was added. The mixture was then stirred at 60 C for 3 h. After removal of the solvents, water and Et2O were added and the aqueous layer was extracted with diethyl ether, cooled in an ice bath then acidified to pH=1 with 1M aqueous HCl. After extraction with ethyl acetate, the organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 50:50) to give the title compound 3 as a mixture of cis/trans isomers (3.48 g, 100% yield) as a colorless oil; deltaH (400 MHz, CDCl3) 10.84 (2H, m, 2*COOH), 3.89 and 3.56 (2*1H, 2*bs, 2*H-4), 2.41-2.18 (2H, m, 2*H-1), 2.10-1.83 (6H, m), 1.74-1.59 (4H, m), 1.58-1.23 (6H, m), 0.88 and 0.87 (2*9H, 2*s, 2*(CH3)3CSi), 0.05 and 0.03 (2*6H, 2*s, 2*(CH3)2Si); deltaC (100 MHz; CDCl3) 181.8 (2*COOH), 70.5 and 66.7 (2*C-4), 42.0 and 41.9 (2*C-1), 34.8 (2*CH2), 32.9 (2*CH2), 27.1 (2*CH2), 23.4 (2*CH2), 26.1 and 26.0 (2*(CH3)3CSi), 18.3 and 18.2 (2*(CH3)3CSi), -4.5 and -4.7 (2*(CH3)2Si).

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zeinyeh, Wael; Radix, Sylvie; Terreux, Raphael; Chemelle, Julie-Anne; Walchshofer, Nadia; Tetrahedron; vol. 72; 27-28; (2016); p. 4032 – 4038;,
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Reference 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

Application of 46004-37-9, 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. 46004-37-9, name is Methyl 4-amino-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-chloro-4-aminobenzoic acid, methyl ester (13.95 g) was suspended in a mixture of water (65 ml) and concentrated hydrochloric acid (15.7 ml). After stirring at room temperature for 10 minutes, the suspension was cooled to 0 C. A solution of sodium nitrite (5.71 g) in water (37 ml) was gradually added over 20 minutes, maintaining a reaction temperature of 0 C. After stirring at 0 C. for 35 minutes, the reaction mixture was partially neutralized by the addition of solid sodium carbonate (3.16 g) to afford a cold solution of the diazonium salt.

The synthetic route of Methyl 4-amino-2-chlorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6831079; (2004); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 135484-83-2,Some common heterocyclic compound, 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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 toluene 12mL solution of methyl 2-amino-4-bromobenzoate 1.2g were added 1-fluoro-4-iodobenzene 1.5mL, cesium carbonate 3.4g, palladium acetate 12mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, palladium acetate 12mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 32mg were added to it, and it was heated and refluxed under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, water was added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 1.0mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B (spherical type), eluent; hexane:ethyl acetate=10:1] to give methyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20g of pale yellow solid. 1H-NMR(DMSO-d6) delta value: 3.86(3H,s),6.94(1H,dd,J=8.6,1.7Hz),7.04(1H,d,J=1.7Hz),7 .24-7.35(4H,m),7.80(1H,d,J=8.6Hz),9.27(1H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-4-bromobenzoate, its application will become more common.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route 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

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;,
Ester – 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 721-63-1 as follows. Computed Properties of C11H11F3O2

General procedure: To a stirred solution of phenyl acetic acid ethyl ester 1a (1 g, 6.09 mmol) in THF (10 mL) was added LiHMDS (9.1 ml, 1 M sol. in THF, 7.31 mmol) at -78 C and the reaction mixture was stirred at this temperature for 30 min. Ethyl-1-imidazole carboxylate 2 (1.2 g, 9.146 mmol) in dry THF (3 ml) was added drop wise to the reaction mixture at -78 C and stirred at rt for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layer was washed with water, saturated brine solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 4% ethyl acetate/pet ether gave the pure compound 3a (1.1 g, 81% yield) as a colorless liquid.

According to the analysis of related databases, 721-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Behera, Manoranjan; Venkat Ragavan; Sambaiah; Erugu, Balaiah; Rama Krishna Reddy; Mukkanti; Yennam, Satyanarayana; Tetrahedron Letters; vol. 53; 9; (2012); p. 1060 – 1062;,
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Related Products of 40876-98-0, 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. 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, This compound has unique chemical properties. The synthetic route is as follows.

5-Aminopyrazole (25 g) and diethyl oxalacetate sodium salt (74.4 g) were dissolved under cooling in 1 N hydrochloric acid. 68.75 ml_ of glacial acetic acid were added and the mixture was stirred at 80C for 14 h. The mixture was cooled to room temperature and the formed precipite was filtered off and titurated in ethyl acetate to give 16.06 g (26%) of the desired product.LC/MS (Method LC1 ): Rt = 0.86 min; m/z = 208.07 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANOFI; Plettenburg, Oliver; Loehn, Matthias; Mendez-Perez, Maria; Hachtel, Stephanie; Podeschwa, Michael; Kannt, Aimo; Ivashchenko, Yuri; Bjergarde, Kirsten; WO2013/60636; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products 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