Tag: M.W=100-200

Application of 3618-04-0, 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.

Example 3 : 8-(3-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-lH-pyrazol-l-yl)-2- oxaspiro [4.5] decan-1-one; Step 1: ethyl 4-(tert-butyldimethyIsilyloxy)cyclohexanecarboxylate.; [124] tert-Butyldimethylsilyl chloride (3.61 g, 0.0240 mol) was added to a solution of 4- hydroxy-cyclohexanecarboxylic acid ethyl ester (3.44 g, 0.0200 mol; ), and lH-imidazole (3.40 g, 0.0499 mol; ) in N,N-Dimethylformamide (5.0 mL, 0.064 mol). The mixture was stirred at the room temperature for 3 hours. The mixture was partitioned between ethyl acetate and water. The ethyl acetate phase was washed with brine, dried over sodium sulfate, filtered, and then concentrated to give oily crude product. Column chromatography eluting with 0-20% ethyl acetate/hexanes gave 5.5 g (96%) of the title compound as colorless oil. 1H-NMR (300 MHz, CD3Cl) delta 4.12 (m, 2H), 3.72 (m, IH), 2.29 (m, IH), 1.93 (m, 2H), 1.65 (m, 2H), 1.56 (m, 2H), 1.48 (m, 2H), .125 (m, 3H), 0.88 (d, 6H), 0.03 (d, 6H).

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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; WO2009/9059; (2009); A1;,
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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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 3-amino-4-methylbenzoate

Methyl-3-amino-4-methyl benzoate (50 g), cyanamide (42 g) was added to ethanol (300 rnL) in a round bottom flask at 25-35C. Concentrated hydrochloric acid (21.2 mL) was added to the reaction mass in a drop-wise manner at 25-35C under nitrogen atmosphere. The reaction mass was heated to 80-85C and, stirred for 6 hours. Then thereaction mass was concentrated under vacuum at less than 50C, then cooled to25-35C. Water (350 mL) was added to the reaction mass, cooled to 0-5C and stirred for 15 mins. Aqueous sodium nitrate solution (51.5 gin 135 ml of DM water) was added to the reaction mass at 0-5C in 45 rnins. The precipitate formed was filtered, washed with DM water, acetone followed by methyl tert-butylether (MTBE), and dried undervacuum at 50-55C to provide the title compound (47.5 g).

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 18595-18-1.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; CHAVA, Satyanarayana; GORANTLA, Seeta Rama Anjaneyulu; INDUKURI, Venkata Sunil Kumar; MOTURU, Venkata Rama Krishna Murthy; JAMJANAM, Srivardhana Rao; SELA, Venkata Purushottama Siva Prasad; WO2015/87343; (2015); A2;,
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Application of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, 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: A 50-mL glass reactor was charged under dry argon at 0 C with 15 mL of THF, and 20 mmol of magnesium powder, 20 mmol of EtAlCl2, and 1.0 mmol of Cp2TiCl2 were added in succession under stirring. After 1 h, 10 mmol of symmetrical acetylene and 20 mmol of ester were added, and the mixture was heated to 60 C and stirred for 6 h at that temperature. When the reaction was complete, the mixture was cooled to 0 C in a stream of argon, 10-15 mL of diethyl ether was added, and the mixture was hydrolyzed with 5 % aqueous HCl. The organic layer was separated, the aqueous layer was extracted with two portions of diethyl ether, and the combined extracts were washed with a solution of NaHCO3 until neutral washings and dried over MgSO4. The product was isolated by vacuum distillation.

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

Reference:
Article; Khafizova; Shaibakova; Chobanov; Gubaidullin; Tyumkina; Dzhemilev; Russian Journal of Organic Chemistry; vol. 51; 9; (2015); p. 1277 – 1281; Zh. Org. Khim.; vol. 51; 9; (2015); p. 1303 – 1307,5;,
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Some common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, molecular formula is C4H3BrO2, 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 3-bromopropiolate

d Methyl 5-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)penta-2,4-diynoate In a manner similar to that of Example 35, the expected product is obtained by coupling 321 mg of methyl bromopropynoate and 200 mg of 6-ethynylselenyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene, in a yield of 28% (70 mg). 1H NMR/CDCl3: 1.23 (s, 6H); 1.33 (s, 6H); 1.67 (s, 4H); 2.35 (s, 3H); 3.79 (s, 3H); 7.13 (s, 1H); 7.65 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 23680-40-2, its application will become more common.

Reference:
Patent; Galderma Research & Development S.N.C.; US6444709; (2002); B1;,
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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 57486-67-6 as follows. Safety of Methyl 2-(2-fluorophenyl)acetate

Example 1A Methyl 3-(3,5-dichloropyridin-2-yl)-2-(2-fluorophenyl)-3-oxopropanoate 28.5 ml (28.5 mmol) of a 1 M solution of LiHMDS in hexane are added to 50 ml of THF at -78 C. A solution of 4.00 g (23.8 mmol) of methyl (2-fluorophenyl)acetate in 10 ml of THF is then added dropwise. The mixture is stirred at -78 C. for 1 h and then 6.00 g (28.5 mmol) of 3,5-dichloro-pyridine-2-carbonyl chloride are added in portions. After a further hour, the mixture is allowed to reach RT and saturated ammonium chloride solution is added dropwise. The mixture is diluted with water and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution and dried over sodium sulfate. The residue after concentration in vacuo is purified by chromatography on silica gel (eluent: dichloromethane/methanol 50:1). 4.46 g (46% of theory) of the desired compound are obtained as a yellowish oil. LC/MS (Method 5): Rt=2.77, 2.82 min; MS (ESIpos): m/z=340 (35Cl2), 342 (35Cl37Cl), 344 (37Cl2) [M+H]+.

According to the analysis of related databases, 57486-67-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; US2010/29653; (2010); A1;,
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Application of 84228-44-4, The chemical industry reduces the impact on the environment during synthesis 84228-44-4, name is Methyl 4-amino-3-chlorobenzoate, I believe this compound will play a more active role in future production and life.

Reference Example 8 Methyl 4-amino-3-chlorobenzoate (5.65 g; synthesised in accordance with Synthesis, 1985, 669) was dissolved in tetrahydrofuran (112 ml) and admixed with a solution of sodium hydrogen carbonate (7.67 g) in water (84.8 ml) and benzyl chloroformate (39.1 ml) and the mixture was stirred under a nitrogen atmosphere at room temperature for 22.5 hours. The reaction mixture was extracted with ethyl acetate and the ethyl acetate layer was washed three times with water and then twice with saturated brine. The ethyl acetate layer was dried over magnesium sulfate and then the solvent was distilled off under reduced pressure, and then the residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:7). A desired fraction was concentrated under reduced pressure and the residue was crystallized from a mixture of ethyl acetate and diisopropyl ether to yield methyl 4-benzyloxycarbonylamino-3-chlorobenzoate (7.51 g) as white crystals. 1H-NMR (CDCl3) delta: 3.91 (3H, s), 5.25 (2H, s), 7.38-7.44 (6H, m), 7.95 (1H, dd, J=8.8 Hz, 2.0 Hz), 8.06 (1H, d, J=2.0 Hz), 8.33 (1H, d, J=8.8 Hz).

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-amino-3-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6495604; (2002); B1;,
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Reference of 23786-14-3, 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. 23786-14-3, name is Methyl 4-methoxyphenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

Will be 100mLThe two reaction bottles were placed in an ice bath at 0 C.Add 2 g (10.0 mmol) of methyl p-methoxyphenylacetate and 20 mL of acetonitrile.Add p-toluenesulfonyl azide 3a (11.0 mmol),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (15.0 mmol) was slowly added.Stir for 5 minutes in an ice bath and place in a microwave reactor.Set power 400W, heating temperature 40 C, heating time 40 min,Turn on the exhaust fan.After the reaction is completed, the mixture is cooled to room temperature, quenched by the addition of ammonium chloride solution, and extracted with dichloromethane and water. The organic phase is collected, dried over anhydrous sodium sulfate, filtered, and evaporated. Chromatographic separation (eluent is petroleum ether (60-90 C) / ethyl acetate, v / v = 100: 1),The target product 1 g (1.75 g, yield: 85%) was obtained as a red solid.The target product was confirmed by nuclear magnetic resonance spectroscopy and high resolution mass spectrometry.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-methoxyphenylacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nanjing Tech University; Gao Zhen; Yi Xiangyan; Huang Fei; Huang He; Yu Yang; Zhang Zhipeng; Xue Lian; Wang Lize; Qiao Nasen; (12 pag.)CN108727216; (2018); A;,
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Electric Literature of 108928-00-3,Some common heterocyclic compound, 108928-00-3, name is Ethyl 2,4-difluorobenzoate, molecular formula is C9H8F2O2, 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.

B. 2,4-Difluoro-5-nitro-benzoic acid ethyl ester. To 2,4-difluoro-benzoic acid ethyl ester (6.4 g, 34 mmol) at 0 C. was added HNO3/H2SO4 (1:1, 10 mL). The resulting solution was allowed to warm to RT and was stirred for 18 h. The reaction mixture was partitioned between H2O and CH2Cl2 (400 mL). The organic layer was washed with brine (200 mL), dried (MgSO4), filtered and concentrated to provide 7.0 g (88%) of the title compound as a white solid. MS (ESI): exact mass calculated for C9H7F2NO4, 231.03; m/z not found. 1H NMR (400 MHz, CDCl3): 8.78 (dd, J=8.3, 7.3, 1H), 7.14 (t, J=9.9, 1H), 4.44 (q, J=7.2, 2H), 1.42 (t, J=7.2, 3H).

The synthetic route of 108928-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allison, Brett D.; Gomez, Laurent; Grice, Cheryl A.; Hack, Michael D.; Morrow, Brian J.; Motley, S. Timothy; Santillan, Alejandro; Shaw, Karen J.; Schwarz, Kimberly L.; Tang, Liu Y.; Venkatesan, Hariharan; Wiener, John J. M.; US2006/223810; (2006); A1;,
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Electric Literature of 1504965-88-1, 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 1504965-88-1 as follows.

The compound (1.83g, 10 mmol) obtained from Preparation Example 83-1 was dissolved in chloroform (50ml), and the solution was cooled to 0. Acetic anhydride (2.36ml, 25mmol) was added thereto, and the solution was stirred for 1 hour at room temperature. Potassium acetate (0.29g, 3mmol) and isopentylnitrite (2.69ml, 20mmol) were added thereto, and the mixture was heated to 70 and stirred for 16 hours. The mixture was cooled to room temperature, diluted with dichloromethane, washed with saturated solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (0.77g, 33%).[1134] NMR:1H-NMR(500HMz, CDCl3); delta 9.00 (d, 1H), 8.14 (s, 1H), 7.46 (d, 1H), 3.98(s, 3H), 2.80 (s, 3H)

According to the analysis of related databases, 1504965-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG LIFE SCIENCES LTD.; LEE, Sung Bae; PAEK, Seung Yup; YOON, Sook Kyung; YOON, Seung Hyun; CHOI, Jeung Soon; WO2014/73904; (2014); 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. 454-31-9, name is Ethyl 2,2-difluoroacetate, A new synthetic method of this compound is introduced below., name: Ethyl 2,2-difluoroacetate

CuO-ZnO-BaO / CNT catalyst 2 prepared in Example 2 was usedA difluoroethanol was prepared by hydrogenation of difluoroacetate,In a stainless steel autoclave, 35 g of ethyl difluoroacetate and 2 g of catalyst 2 were placed,Closed reactor, the use of 0.5MPa hydrogen replacement kettle air, the introduction of hydrogen pressure of 2MPa,Heating up to 110 C with stirring,Reaction 4 h. Cooling down, until the temperature dropped to 25 after the pressure, open the reactor,After the reaction solution was taken out, the catalyst was separated from the reaction solution, the filtrate was distilled at atmospheric pressure and the pellets were collected at 97 to 99 C,21.5 g of difluoroethanol was obtained, the yield was 93.3%, and the purity was 99%.

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; Shandong Dongyue PolymerMaterial Co., Ltd.; CHEN, YUE; LUO, YONGZHEN; BI, ZUOWEI; (6 pag.)CN105461512; (2016); A;,
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