Tag: M.W=100-200

Some common heterocyclic compound, 762-42-5, name is Dimethyl but-2-ynedioate, molecular formula is C6H6O4, 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. Formula: C6H6O4

General procedure: At room temperature, organic carbonyl acid 3 (R-COOH, 0.5 mmol) was added into a reaction tube equipped with a small magnet. Then a solution of tertiary amine 1 (R1CH2-NR2R3, 0.5 mmol ) in DCM (2.5 mL) was added dropwise in 2 min. After the mixture was stirred at room temperature for a few minutes, 1 equivalents of dimethyl acetylenedicarboxylate (DMAD, 2) was added. The reaction was stirred overnight at room temperature, and then monitored by TLC with silica gel coated plates. After being stirred for 14 h, the solvent was removed and the residue was purified by a flash column chromatography with silica gel with ethyl acetate/hexane (1:25-30) as eluent to give the desired products 4, 5, and 7. Most of compounds are known and confirmed by NMR, ESI-MS, IR.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 762-42-5, its application will become more common.

Reference:
Article; Shen, Hao; Lu, Xing; Jiang, Ke-Zhi; Yang, Ke-Fang; Lu, Yixin; Zheng, Zhan-Jiang; Lai, Guo-Qiao; Xu, Li-Wen; Tetrahedron; vol. 68; 43; (2012); p. 8916 – 8923;,
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Synthetic Route of 87661-20-9, A common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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.

Step 1: A solution of n-butyl lithium in hexane (1.4M, 45.75 mL, 0.07 mol) was added drop wise to a solution of freshly distilled diisopropylamine (10.2 mL, 0.06 mol) in dry THF (200 mL) at -60 C. under nitrogen atmosphere. The reaction mixture was slowly warmed to -20 C. and stirred for 30 min. The reaction mixture was re-cooled to -60 C. and cyclopropanecarboxylic acid tert-butyl ester (9.48 g, 0.06 mol) added drop wise over a period 30 min. Reaction mixture was slowly warmed to -20 C. and stirred for 30 min. To the re-cooled (-60 C.) reaction mixture was added drop wise 1,10-dibromodecane (20.0 g, 0.06 mol) in dry THF (20 mL) and DMPU (1.79 g, 0.01 mol). Then the temperature was allowed to reach room temperature and stirred at same temperature over a period of 16 h The resulting reaction mixture was quenched with saturated NH4Cl (500 mL) at 0 C. and the reaction mixture was extracted with ethyl acetate (300 mL¡Á3). The organic phases were combined, dried over anhydrous Na2SO4 and volatiles were evaporated under reduced pressure to yield a pale yellow liquid which was purified through silica gel (230-400) column (0.5% ethyl acetate in petroleum ether) to give product as colorless oil 8.0 g (33%).1H NMR (300 MHz, DMSO-d6) delta (ppm): 0.62-0.64 (m, 2H), 0.94-0.98 (m, 2H), 1.25 (bs, 12H), 1.37 (s, 9H), 1.39-1.43 (m, 4H), 1.73-1.80 (m, 2H), 3.52 (t, J=6.6 Hz, 2H).

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; KAREUS THERAPEUTICS, SA; US2012/71528; (2012); A1;,
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Some common heterocyclic compound, 1462-12-0, name is Diethyl 2-ethylidenemalonate, molecular formula is C9H14O4, 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. Product Details of 1462-12-0

General procedure: To a mixture of alkene 1 (0.5 mmol), aldehyde 2 (2.5 mmol), and FeCl2 (1.6 mg, 0.0125 mmol), acetonitrile (3.0 mL) was added under nitrogen at room temperature. Then tert-butyl hydroperoxide 3 (TBHP, 2.0 mmol, 5-6 M in decane) was dropped into the mixture under nitrogen at room temperature. The resulting mixture was stirred under 85 oC for 1 h. The temperature of reaction was cooled to room temperature. The resulting reaction solution was directly filtered through a pad of silica by ethyl acetate. The solvent was evaporated in vacuo to give the crude products. NMR yields are determined by 1H NMR using dibromomethane as an internal standard. Solvent was evaporated and the residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether as eluent to afford the pure product 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1462-12-0, its application will become more common.

Reference:
Article; Liu, Kaisheng; Li, Yuanming; Zheng, Xiaojian; Liu, Weiping; Li, Zhiping; Tetrahedron; vol. 68; 50; (2012); p. 10333 – 10337;,
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Adding a certain compound to certain chemical reactions, such as: 7148-50-7, name is 5-Methyl-5-propyl-1,3-dioxan-2-one, 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 7148-50-7, Computed Properties of C8H14O3

Step 4; 2-(Hydroxymethyl)-2-methylpentyl isopropylcarbamate: At ambient temperature, several batches of propan-2-amine hydrochloric acid salt (171 mg, 1.80 mmol, 1.50 equiv.) was added to a solution of 5-methyl-5-propyl-1,3-dioxan-2-one (200 mg, 1.20 mmol, 1.00 equiv) in triethylamine (20 mL). The mixture was maintained at about 90 C. for about 2 hours. The mixture was then concentrated in vacuo and the resulting residue was diluted with water (50 mL). Following standard extractive workup with ethyl acetate, the crude residue was purified by silica gel column chromotagraphy (methanol/dichloromethane (1:50)) to afford the title product as a brown oil (220 mg, 1.01 mmol). 1H NMR (300 MHz, CDCl3) delta: 4.58 (s, 1H), 3.94 (s, 2H), 3.82 (m, 1H), 3.28 (dd, J=12.0, 11.7 Hz, 2H), 2.36 (br, 1H), 1.32 (m, 4H), 1.19 (d, J=6.3 Hz, 6H), 0.98 (t, J=6.3, 7.2 Hz, 3H), 0.87 (s, 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, 5-Methyl-5-propyl-1,3-dioxan-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; US2010/76074; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 23676-08-6, name is Methyl 4-ethoxybenzoate, 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 23676-08-6, COA of Formula: C10H12O3

General procedure: Hydrazine hydrate 64% (v/v) (30.0 mL, 0.33 mol) was heated up to 50-60 C. The methyl ester 3 (0.01 mol) was added and the mixture was heated at reflux for 10 min. The cooling was performed sequentially in water bath, followed by ice bath and dry ice-ethanol bath. The precipitate was filtered and washed with cold water.

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, Methyl 4-ethoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ishii, Marina; Jorge, Salomao Doria; De Oliveira, Alex Alfredo; Palace-Berl, Fanny; Sonehara, Ieda Yuriko; Pasqualoto, Kerly Fernanda Mesquita; Tavares, Leoberto Costa; Bioorganic and Medicinal Chemistry; vol. 19; 21; (2011); p. 6292 – 6301;,
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Adding a certain compound to certain chemical reactions, such as: 123-29-5, name is Ethyl nonanoate, 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 123-29-5, Recommanded Product: 123-29-5

EXAMPLE 4 STR11 1-Methoxy-7-(4-pentenyloxy)heptane Sodium hydride (665 mg, 17 mmol, washed three times with hexane) was treated with the title product of Example 3 (2.0 g, 14 mmol) in 90 mL of tetrahydrofuran at reflux for one hour. A solution of 5-bromopentene (2.0 g, 14 mmol) in 50 mL of tetrahydrofuran was added dropwise and refluxing continued for 20 hours. After cooling to room temperature, 50 mL of water was added, the layers separated and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Chromatography of the crude residue on silica gel using 50–50 ethyl acetate-heptane as eluant gave the title compound (485 mg) as a yellow oil and the structure verified by NMR.

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; G. D. Searle & Co.; US5859052; (1999); A;; ; Patent; G. D. Searle & Co.; US5599947; (1997); A;,
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Adding a certain compound to certain chemical reactions, such as: 3070-71-1, name is Methyl 2-benzylacrylate, 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 3070-71-1, Quality Control of Methyl 2-benzylacrylate

(1) Compound (7) (239.7 mg, 0.93 mmol) obtained in Example 7 was dissolved in dehydrated toluene (5.0 mL), Compound (4) (R2=Bn, R=Me) (530 mg, 3.0 mmol) synthesized according to a method of Basavaiah et al. (Tetrahedron Lett. Vol. 42, 477-479 (2001)) was added to the solution, and the mixture was stirred for 12 hr at 60 C. under nitrogen atmosphere and further for 2 hr at 90 C. The reaction mixture was concentrated in vacuo, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1) to obtain a crude body of Compound (8) (R1=Ph(CH2)2, R2=Bn, R=Me).

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, Methyl 2-benzylacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TEIJIN PHARMA LIMITED; US2005/182032; (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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: tert-Butyl cyclopropanecarboxylate

Example 21A tert-Butyl 1-(3-bromo-4-chlorobenzyl)cyclopropanecarboxylate [0434] THF and cooled to -30 C. 400 ml (1.0 mol) of n-butyllithium solution (2.5 M in hexane) were added dropwise. The resulting mixture was warmed to 0 C. and then cooled to -70 C. A solution of 94.8 g (0.667 mol) of tert-butyl cyclopropanecarboxylate in 750 ml THF was added to the reaction solution, with the temperature being kept below -60 C. After 4 h of stirring at -60 C., a solution of 208.6 g (0.733 mol) of 2-bromo-4-(bromomethyl)-1-chlorobenzene in 550 ml of THF was added, the temperature again being kept below -60 C. The reaction mixture was slowly warmed to RT overnight, and saturated aqueous ammonium chloride solution was then added carefully. After phase separation, the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ dichloromethane 4:1). This gave 95.5 g (41.4% of theory) of the title compound. [0436] GC-MS (Method 1): Rt=6.54 min; m/z=288/290 (M-C4H8)+. [0437] LC-MS (Method 3): Rt=1.65 min; m/z=288/290 (M-C4H8)+.

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; Lampe, Thomas; Hahn, Michael; Stasch, Johannes-Peter; Schlemmer, Karl-Heinz; Wunder, Frank; El Sheikh, Sherif; Li, Volkhart Min-Jian; Becker-Pelster, Eva Maria; Stoll, Friederike; Knorr, Andreas; US2015/152050; (2015); A1;,
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Application of 66315-23-9,Some common heterocyclic compound, 66315-23-9, name is Ethyl 3-amino-4-(methylamino)benzoate, molecular formula is C10H14N2O2, 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.

Step 2-1-1 Ethyl 1,2-dimethyl-1H-benzimidazole-5-carboxylate Ethyl 3-amino-4-methylaminobenzoate (1.00 g, 5.15 mmol) prepared in the Step 1-1-3 was dissolved in acetic anhydride (4 ml), and the mixture was heated under reflux for 19 hours. After being allowed to cool, the mixture was neutralized with a saturated sodium bicarbonate solution and subjected to extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (1.15 g, quantitative) as a light-brown oily substance. 1H-NMR (CDCl3) delta: 8.39 (d, J=1.5 Hz, 1H), 7.98 (dd, J=1.5, 8.5 Hz, 1H), 7.28 (d, J=8.5 Hz, 1H), 4.39 (q, J=6.9 Hz, 2H), 3.75 (s, 3H), 2.62 (s, 3H), 1.41 (t, J=6.9 Hz, 3H) Mass, m/z: 218 (M+), 173 (base)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-amino-4-(methylamino)benzoate, its application will become more common.

Reference:
Patent; Uchida, Hiroshi; Asagarasu, Akira; Matsui, Teruaki; US2013/79306; (2013); A1;,
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These common heterocyclic compound, 35472-56-1, name is Ethyl 2-(methylamino)benzoate, 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. Quality Control of Ethyl 2-(methylamino)benzoate

EXAMPLE 26 3-[2-(cis-6-Methoxy-2,3,3a,4,5,9b-hexahydro-[1H]-benz[e]isoindol-1-yl)ethyl]-1-methyl-quinazoline-2,4(1H,3H)-dione hydrochloride N-Methyl-2-carboethoxyaniline (5.0 g, 28 mmol) was treated with 2-chloroethylisocyanate (2.86 mL, 28 mmol) at reflux in toluene for 18 hours. The reaction was cooled to 25 C., and the crystalline product was collected by filtration to yield the intermediate 1-methyl-3-(2-chloroethyl)-quinazoline-2-4-dione.

The synthetic route of Ethyl 2-(methylamino)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott Laboratories; US5521181; (1996); A;,
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