Tag: M.W=100-200

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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of (E)-Ethyl 4-bromobut-2-enoate

Intermediate 26 Ethyl (2E)-4-(5-bromo-2-nitrophenoxy)but-2-enoate 5-Bromo-2-nitrophenol (10 g, 45.9 mmol) and K2CO3 (8.24 g, 59.6 mmol) were suspended in NMP (81 mL) (a bright red suspension) and ethyl 4-bromocrotonate (10.26 mL, 59.63 mmol) was added dropwise at room temperature. The reaction was stirred at room temperature over night (20 h). The mixture was poured into ice/water (500 mL) and stirred for 30 min. The precipitate was collected by filtration and washed with water (2*200 mL), air dried for 10 min and then washed with heptane (200 mL). Heptane (200 mL) was added to the solid and stirred for 1 h. The solid was filtered off, washed with heptane (2*50 mL) and dried in vacuo to afford a beige solid. The title compound (15.0 g, 99%) was obtained and was used without further purification. 1H NMR (500 MHz, CDCl3) delta 1.32 (t, 3H), 4.24 (q, 2H), 4.84 (dd, 2H), 6.31 (dt, 1H), 7.04 (dt, 1H), 7.18-7.26 (m, 2H), 7.80 (d, 1H). MS m/z 298 (M-H)-.

According to the analysis of related databases, 37746-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; O’MAHONY, Gavin; KOSSENJANS, Michael; EDMAN, Karl; KAJANUS, Johan; HOGNER, Karl Anders; CORNWALL, Philip; TURNER, Andrew; (35 pag.)US2015/376170; (2015); A1;,
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These common heterocyclic compound, 4891-38-7, name is Methyl Phenylpropiolate, 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. Application In Synthesis of Methyl Phenylpropiolate

EXAMPLE 24 [3,5-diphenylisoxazole-4-yl]methyl carboxylate The benzonitrile oxide (0.98 mmoles) just prepared is added to the methyl 3-phenylpropiolate (157 mg, 0.98 mmoles) in anhydrous methylene chloride (5 ml) kept stirring at ambient temperature in an atmosphere of N2. The reaction mixture is kept stirring for 12 h, then blocked by adding H2O, The phases are separated and the aqueous phase is extracted with methylene chloride. The organic phases are combined, dried with anhydrous Na2SO4 and the solvent is distilled in a vacuum. Chromatography is performed on silica gel (eluent:petroleum ether/ethyl acetate=10:1). 184 mg of product are obtained (67% yield). M.p. 102.5-104.8 C. FT-IR (KBr): 3062, 2958, 1729, 1610, 1593, 1573, 1494, 1448, 1408, 1320, 1237, 1188, 1120, 1076, 1043, 941, 806, 768, 726, 697 cm-1. 1H NMR (300 MHz, CDCl3, delta): 7.96-7.88 (m, 2H, aromatic protons); 7.70-7.63 (m, 2H, aromatic protons); 7.56-7.46 (m, 6H, aromatic protons); 3.72 (s, 3H, CH3). 13C NMR (75 MHz, CDCl3, delta): 172.7, 163.2, 163.1, 131.6, 130.2, 129.1, 128.9, 128.8, 128.7, 128.6, 127.1, 102, 52.2. GC-MS (70 eV) m/z (rel.int.): 279 (M+, 79), 278 (17), 251 (6), 220 (5), 202 (7), 143 (10), 105 (100), 77 (47), 51 (9). Anal. Calc: for C17H13NO3: C, 73.11; H, 4.69; N, 5.02. Found: C, 73.06; H, 4.67; N, 5.06.

The synthetic route of Methyl Phenylpropiolate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Scilimati, Antonio; Vitale, Paola; Di Nunno, Leonardo; Patrignani, Paola; Tacconelli, Stefania; Capone, Marta Luciana; US2009/181970; (2009); A1;,
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Synthetic Route of 685-88-1, 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. 685-88-1, name is Diethyl fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

NaH (0.88 g, 22 mmol 60% in mineral oil) was washed free from the oil with hexanes (3 × 10 mL) and was suspended in dry DMF (30 mL). Diethyl fluoromalonate (2.85 g, 16 mmol) dissolved in dry DMF (10 mL) was added dropwise while cooled in ice. After stirring for 10 minutes, 1-fluoro-2-nitrobenzene (2.10 g, 15 mmol) in dry DMF (10 mL) was added and the mixture was heated to 90 C for 18 hours. After cooling to room temperature, the mixture was poured into water (300 mL), acidified with concentrated HCl (2 mL) and extracted with ether (3 × 70 mL). The combined extracts were washed with saturated NaHCO3 solution (2 × 50 mL) and brine (1 × 50 mL) and dried over Na2SO4. After evaporation of the solvent under reduced pressure an orange oil was obtained that was purified by Kugelrohr distillation (8 mbar, 200 C) to afford diethyl 2-fluoro-2-(2-nitrophenyl)malonate (3, 3.21 g, 71%) as an orange solid. M.p. 48-49 C; IR (neat, cm-1) 2996, 1755, 1530, 1276, 1103; deltaH (CDCl3, 400 MHz) 1.33 (6H, t, J 7.1, CH3), 4.31 – 4.43 (4H, m, CH2), 7.57 – 7.63 (2H, m, Ar-H), 7.66 – 7.71 (1H, m, Ar-H), 8.04 (1H, d, J 8.0, Ar-H); deltaF (CDCl3, 376 MHz) – 152.98 (s, C-F); deltaC (CDCl3, 100 MHz) 14.01 (s, CH3), 63.55 (s, CH2), 94.05 (d, 1JCF 198.7, C-F), 125.87 (s, Ar), 128.54 (s, Ar), 128.66 (s, Ar), 128.89 (s, Ar), 130.97 (s, Ar), 133.30 (s, Ar), 164.68 (d, 2JCF 25.1, COO); m/z (ASAP): 226.0 (85%, [M-CO2Et]+), 134.0 (100%).

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, Diethyl fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Harsanyi, Antal; Sandford, Graham; Yufit, Dmitri S.; Howard, Judith A.K.; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1213 – 1219;,
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Related Products of 35418-07-6, A common heterocyclic compound, 35418-07-6, name is Methyl 3-(4-aminophenyl)propanoate, molecular formula is C10H13NO2, 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.

EXAMPLE XXVII 1-[4-[2-(Methoxycarbonyl)ethyl]phenyl]-4,5-dimethyl-3H-imidazol-2-one 2.4 g of N-[4-[2-(methoxycarbonyl)ethyl]phenyl]-urea ?melting point: 152-154 C. (sintering from 145 C.); prepared from methyl 3-(4-aminophenyl)propionate by reacting with potassium cyanate in the presence of glacial acetic[acid]and 2.9 g of acetoin are heated to 180 C. for 1 hour under nitrogen. The reaction mixture is cooled stirred with ice water and the solid substance is suction filtered. The product is washed with water and diethylether and dried at 100 C. Yield: 1.6 g (54% of theory) Melting point: 176-181 C. Rf value: 0.11 (Silica gel; cyclohexane/ethyl acetate=2:8)

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; Karl Thomae GmbH; US5681841; (1997); A;,
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Electric Literature of 383-62-0, The chemical industry reduces the impact on the environment during synthesis 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, I believe this compound will play a more active role in future production and life.

To a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.5 g, 2.58 mmol, 1 eq) in DMF (5 mL) was added ethyl 2-chloro-2,2-difluoro-acetate (490.20 mg, 3.09 mmol, 392.16 uL, 1.2 eq) and K2CO (712.26 mg, 5.15 mmol, 2 eq). The mixture was stirred at 60 C for 16 h. The reaction mixture was poured into H2O 10 mL, and extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine (10 mL x 2), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound (0.3 g, crude) as yellow solid, which was used into the next step without further purification. The structure was confirmed by 1H NMR and HOSEY.

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 2-chloro-2,2-difluoroacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MARINEAU, Jason, J.; ZAHLER, Robert; CIBLAT, Stephane; WINTER, Dana, K.; KABRO, Anzhelika; ROY, Stephanie; SCHMIDT, Darby; CHUAQUI, Claudio; MALOJCIC, Goran; PIRAS, Henri; WHITMORE, Kenneth, Matthew; LUND, Kate-Iyn; SINKO, Bill; SPROTT, Kevin; (418 pag.)WO2018/13867; (2018); A1;,
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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 5335-05-7 as follows. category: esters-buliding-blocks

Under nitrogen protection,The racemic mixture of 3- (indol-3-yl) -butyric acid or S-3-iv)(0 · 20 g, 1 mmol)And triethylamine (0 · 10 g, 1 mmol)Dissolved in DMF solution (6ml) solution at room temperature for 5min,Then methyl chlorobenzoate (0.17 g, 1 mmol),The reaction at room temperature 24h, after the reaction was added ethyl acetate 50ml,The ethyl acetate layer was washed with water (80 ml X 3) and the ethyl acetate layer was dried over anhydrous Na 2 SO 4. After the solvent was removed by column chromatography, the target compound 3- (3-indol-3-yl) Methyl ester (0.23 g, 70%),Which is a racemic mixture or (S) isomer.

According to the analysis of related databases, 5335-05-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Bio-technology Institute; Liu Zongying; Li Zhuorong; Jin Jie; Zhu Juntai; (111 pag.)CN103664996; (2017); B;,
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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. 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 56741-34-5

General procedure: To a solution of 11a (500 mg, 1.85 mmol) in acetone (10 mL) was added 12 (380 mg, 1.85 mmol) and pyridine (0.45 mL, 5.54 mmol).The mixture was stirred at 55 C for 1 h. The mixture was concentrated,diluted with ethyl acetate and washed with 1M HCl and brine twice.Then, the ethyl acetate layer was dried over anhydrous sodium sulfate andconcentrated to give the crude product. The crude product was purified bysilica column eluting with petroleum ether/ethyl acetate (5/1-2/1) to givethe desired product (0.33 g, yield 44.3%) as grey solid

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 56741-34-5.

Reference:
Article; He, Yulong; Dou, Huixia; Gao, Dingding; Wang, Ting; Zhang, Mingming; Wang, Heyao; Li, Yingxia; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
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25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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. category: esters-buliding-blocks

[0511] 5-Chlorosalicylaldehyde (20.02 g, 0.128 mole) and ethyl 4,4, 4-trifluorocrotonate (23.68 g, 0.14 mole) were dissolved in anhydrous DMF, warmed to 60 C and treated with anhydrous K2CO3 (17.75 g, 0. 128 mole). The solution was maintained at 60 C for 20 hours, cooled to room temperature, and diluted with water. The solution was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous MGS04, filtered and concentrated in vacuo to afford 54.32 g of an oil. The oil was dissolved in 250 mL of methanol and 100 mL of water, whereupon a white solid formed that was isolated by filtration. The resulting solid was washed with water and dried in vacuo, to afford the ester as a yellow solid (24.31 g, 62%): mp 62-64 C. 1H NMR (CDC13/90 MHz) 7.64 (s, 1H), 7.30-7. 21 (m, 2H), 6.96 (d, 1H, J= Hz), 5.70 (q, 1H, J= Hz), 4.30 (q, 2H, J= 7.2 Hz), 1.35 (t, 3H, J=7.2 Hz).

The synthetic route of 25597-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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Electric Literature of 37466-90-3, These common heterocyclic compound, 37466-90-3, name is Ethyl 3,4-diaminobenzoate, 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.

General procedure: To a mixture of 2-pyridine aldehyde (5a, 107 mg, 1mmol) and 1,2-diaminobenzene (6a, 108 mg, 1 mmol) in ethanol (25 mL)was added an aqueous solution of sodium pyrosulfite (1.52g, 8 mmol, 5 mL) and refluxed for 4 to 6 h, until the TLC indicated that reaction was completed. The reaction mixture was concentrated under vacuum and the residue was dissolved in CHCl3 (2 x15 mL) and washed with water. The combined organic phases were dried over anhydrousNa2SO4, filtered and the solvent was removed under vacuumand purified by column chromatography (70% EtOAc-hexane) to afford compound 7a as a brown solid.

The synthetic route of 37466-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Pogula, Praveen Kumar; Khan, Mohammed Naseer Ahmed; Seshadri, Bobburi Naga; Sreekanth, Kokkonda; Medicinal Chemistry; vol. 9; 5; (2013); p. 651 – 659;,
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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 36692-49-6 as follows. Product Details of 36692-49-6

A mixture of methyl 3,4-diaminobenzoate (8, 830 mg, 5 mmol) and 4-methoxy benzaldehyde (9a, 680 mg, 5 mmol) in ethanol (25 mL) was heated with an aqueous solution of sodium pyrosulfite (1.42 g, 1.5 mmol, 5 mL) and then refluxed for 4-6 h, until TLC indicated that the reaction was complete. The ethanol was evaporated under vacuum and the residue was dissolved in CHCl3 (2 * 15 mL) and washed with water. The combined organic phases were dried over anhydrous Na2SO4, and the solvent was removed under vacuum and purified by column chromatography MeOH-CH2Cl2 (0.5:9.5) to obtain the pure product 10a as a white solid (952 mg, 68%); mp: 231-234 C; 1H NMR (500 MHz, CDCl3): delta 8.28 (s, 1H), 8.12 (d, J = 9.1 Hz, 2H), 7.92 (d, J = 9.0 Hz, 1H), 7.12 (d, J = 8.3 Hz, 1H), 6.98 (d, J = 8.3 Hz, 2H), 3.94 (s, 3H), 3.85 (s, 3H); MS (ESI): m/z 283 [M + H]+.

According to the analysis of related databases, 36692-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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