Tag: M.W=200-300

Reference of 59227-79-1,Some common heterocyclic compound, 59227-79-1, name is Ethyl 4-(4-chlorophenoxy)butanoate, molecular formula is C12H15ClO3, 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: Hydrazine hydrate (0.045 mol) was added to the solution of compounds 3a-l (0.03 mol) in ethanol (20 ml) and stirred the reaction mixture at room temperature for 5 h. Reaction completion was monitored by thin layer chromatography using hexane:ethylacetate (2:1) as the mobile phase and allowed to stand overnight. The white crystals 4a-l formed were filtered, washed and after drying recrystallized from ethanol. 4-(4-Chloro-phenoxy)-butyric acid hydrazide (4b) Yield 90%; mp 85-87 C; FT-IR (KBr, cm-1): 3315 (NH2), 3220 (NH), 1672 (C=O); 1H NMR (CDCl3): delta 2.26 (m, 2H, CH2), 2.75 (t, 2H, COCH2), 3.85 (d, 2H, NH2), 4.07 (t, 2H, OCH2), 6.88 (d, J = 8.80 Hz, 2H, Ar-H), 7.27 (d, J = 8.85 Hz, 2H, Ar-H), 8.40 (t, 1H, NH); LC-MS m/z 229 (M + 1). Anal. Calcd. for C10H13ClN2O2: C, 52.52; H, 5.73; N, 12.25. Found: C, 52.43; H, 5.75; N, 12.39%.

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

Reference:
Article; Al-Ghorbani, Mohammed; Vigneshwaran; Ranganatha, V. Lakshmi; Prabhakar; Khanum, Shaukath Ara; Bioorganic Chemistry; vol. 60; (2015); p. 136 – 146;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

90942-47-5, name is Methyl 5-(aminomethyl)-2-chlorobenzoate hydrochloride, 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

To a solution of methyl 5-(aminomethyl)-2-chlorobenzoate hydrochloride (2.50 g,10.59 mmol) in THF (20 mL) were added DIPEA (4.78 g, 37.07 mmol) andisobutyryl chloride (1.70 g, 15.89 mmol). The reaction mass was stirred at RT for 2 h. After completion of the reaction, the reaction mixture was diluted with EtOAc, washed with water and brine, dried over Na2 SO4 and concentrated to afford 1.2 g of the desired product. ?H NIVIR (300 IVIHz, DMSO-d6): 8.35 (t, 1H), 7.66 (s, 1H),7.55-7.52 (d, J= 8.1 Hz, 1H), 7.43-7.40 (d, J 8.1 Hz, 1H), 4.26 (d, J 5.7 Hz, 2H),3.85 (s, 3H), 2.44 (m, 1H), 1.02 (d, J= 6.9 Hz, 6H); MS [M+H]: 270.12.

The synthetic route of 90942-47-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; TAMBE, Macchindra Sopan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2015/59618; (2015); 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. 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 2-bromo-4-methylbenzoate

[0202] A mixture of the above product (0.600 g, 1.57 mmol), methyl 2-bromo-4-methylbenzoate (0.395 g, 1.72 mmol), potassium carbonate (0.541 g, 3.92 mmol), triphenylphosphine (0.016 g, 0.06 mmol), and palladium acetate (3.5 mg, 0.01 mmol) in 7 mL of THF and 0.2 mL of water was heated in a sealed flask at 100 C. overnight. The mixture was then cooled and partitioned between ethyl acetate and water. The organic extract was washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 0-10% ethyl acetate and hexane to provide methyl 5-methyl-4′-{(1R)-1-[(4-methyl-3-nitropyridin-2-yl)amino]ethyl}-1,1′-biphenyl-2-carboxylate that gave a proton NMR spectrum consistent with theory and a mass ion (ES+) of 406.2 for M+H+.

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; Kuduk, Scott D.; Bock, Mark G.; Feng, Dong-Mei; Wai, Jenny Miu-Chun; US2004/34064; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 1731-79-9, 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. 1731-79-9, name is Dimethyl dodecanedioate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 8 A condensation solution in an amount of 113.2 g (confirmed by quantitative analysis, after acidification of a part, that the solution contains 25.65 g of the condensation product and 80.84 g of the unreacted ester) prepared from dimethyl 1,12-dodecanedioate (105.00 g, 406.4 mmol), gamma-butyrolactone (8.75 g, 101.6 mmol), and a 28-wt % sodium methoxide in methanol solution (19.60 g, 101.6 mmol) was heated to 50 C. while being stirred. Into the solution, 550 g of n-hexane was added and was stirred while being cooled to 20 C. to form a suspension. The suspension was separated into a precipitate and a supernatant liquid using a pressure filter. The filtration residue was thoroughly washed with n-hexane. The resulting filtration residue in an amount of 35.55 g was poured into 49.8 g (50.8 mmol) of an aqueous 10% phosphoric acid solution. Further, water (350 g) and 1,4-dioxane (250 g) were added, and the mixture was allowed to react for 5 hours at 100 C. The solution was separated into two layers. The organic layer was separated and the aqueous layer was extracted with toluene. The organic layer was mixed with the toluene extract and washed with water, and then the solvent was removed by distillation. As a result, 26.6 g of a crystal product was obtained. After isolation and purification, the crystal product was identified as methyl 15-hydroxy-12-keto-pentadecanoate corresponding to the compound represented by the general formula (7). 1H-NMR (600 MHz, TMS, CDCl3) 1.28 (12H, m, CH2-4~9), 1.57 (2H, tt, J=7.3, 7.2, CH2-10), 1.61 (2H, tt, J=7.3, 7.0, CH2-3), 1.84 (2H, tt, J=6.7, 6.3, CH2-14), 2.30 (2H, t, J=7.5, CH2-2), 2.43 (2H, t, J=7.5, CH2-11), 2.56 (2H, t, J=6.9, CH2-13), 3.65 (2H, t, J=6.1, CH2-15), 3.67 (3H, s, CH3). 13C-NMR (150 MHz, CDCl3) 23.86 (CH2-10), 24.92 (CH2-3), 26.50 (CH2-14), 29.09~29.36 (CH2-4~9), 34.08 (CH2-2), 39.48 (CH2-13), 42.92 (CH2-11), 51.40 (CH3), 62.33 (CH2-OH), 174.30 (C(=O)O), 211.76 (C=O).

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, Dimethyl dodecanedioate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Soda Aromatic Co., Ltd.; US6291688; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 32454-36-7, A common heterocyclic compound, 32454-36-7, name is Ethyl 2-(4-bromophenyl)-2-methylpropanoate, molecular formula is C12H15BrO2, 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 B: 2-(4-Bromophenyl)-2-methylpropan-l-olTo a solution of 2-(4-bromophenyl)-2-methylpropanoate (8.9 g, 33 mmol) in THF(100 mL) under nitrogen was added LiAltL; (1.6 g, 43 mmol) in portions at 0 C. The resulting solution was stirred at 0 C for 1 hour before the addition of saturated aqueous NFLjCl (50 mL). The mixture was then extracted with EtOAc (3×80 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel with 2-5 % EtOAc/hexane to afford 2-(4-bromophenyl)-2- methylpropan-l-ol as a colorless oil. MS ESI: [M+H]+ m/z 229, 231 ; 1H NMR (400 MHz, CDC13) delta 7.47 (d, J= 6.8 Hz, 2H), 7.28 (d, J= 6.8 Hz, 2H), 3.61 (s, 2H), 1.58 (s, 6H).

The synthetic route of 32454-36-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BRUBAKER, Jason; DINSMORE, Christopher J.; HOFFMAN, Dawn Marie; JUNG, Joon; LIU, Duan; PETERSON, Scott; SIU, Tony; TORRES, Luis E.; ZHANG, Hongjun; WEI, Zhongyong; SHI, Feng; WO2013/40863; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 1731-79-9, A common heterocyclic compound, 1731-79-9, name is Dimethyl dodecanedioate, molecular formula is C14H26O4, 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 4 [00088] The following Example describes the transesterification of dimethyl dodecanedioate using p-toluenesulfonic acid catalyst and the preparation of DDDA diester using a mixture of 50 mole % Exxal 13 and 50 mole % 1H, 1H, 5H-octafluoro-1-pentanol. [00089] A mixture of 51.68 g dimethyl dodecanedioate (0.2 mole), 41.58 g Exxal 13 (0.21 mole), 48.73 g 1H, 1H, 5H-octafluoro-1-pentanol (0.21 mole), and 0.38 g p-toluenesulfonic acid was heated, and methanol distilled off. When the reaction temperature reached 198 C., GC analysis showed the dimethyl dodecanedioate to be essentially gone, indicating that the reaction had gone nearly to completion. After cooling, the product was washed with brine, 1% aqueous NaOH, and water, then treated with basic alumina and filtered. The final acid number was 0.1 mg KOH/g. [00090] The same basic procedure was used to prepare other diesters, listed in Table 6. The non-fluorinated alcohol was Exxal 13 in all cases.[TABLE-US-00007] TABLE 6 DDDA diesters prepared according to Example 4. Mole fractionAcid PartiallypartiallynumberWt % FWt % FPrepara-Fluorinatedfluorinated(mg(elemental(bytionalcoholalcoholKOH/g)analysis)NMR) 30Telomer0.025 1.121.24 alcohol-L311H, 1H, 5H-0.50.1 octafluoro-1- pentanol321H, 1H, 2H,0.50.1 2H-perfluoro- 1-octanol331H, 1H0.50.1 heptafluoro- 1-butanol341H, 1H-0.50.1 perfluoro-1- octanol35Telomer0.0252 alcohol36Telomer0.0250.521.451.63 alcohol

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; E. I. du Pont de Nemours and Company; US6734320; (2004); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 697762-67-7,Some common heterocyclic compound, 697762-67-7, name is Methyl 5-bromo-2-chloro-3-methoxybenzoate, molecular formula is C9H8BrClO3, 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.

The compound (74.80 g, 0.27 mol) obtained in Step 4 was dissolved in dichloromethane (300 ml) and 1M boran tribromide/dichloromethane solution (700 ml, 0.70 mol) was added dropwise at 10C or below. After completion of the addition, the mixture was stirred at room temperature for 1.5 hrs. The reaction mixture was added to ice water (1500 ml) and the precipitated solid was collected by filtration. The filtrate was partitioned, and the aqueous layer was extracted with ethyl acetate (200 ml). The organic layers were combined and concentrated under reduced pressure. The solid collected by filtration and the residue were dissolved in diethyl ether (1000 ml) and 1N aqueous sodium hydroxide solution (1000 ml) was added for extraction. 2N Hydrochloric acid (500 ml) was added to the aqueous layer. The mixture was stirred and extracted with ethyl acetate (800 ml). The mixture was partitioned and the organic layer was washed successively with water and saturated brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give an object product (63.83 g, yield 95%) as a beige solid.1H NMR(DMSO-d6 300MHz) (delta) ppm: 7.23 (1H, d, J=2.4Hz), 7.28 (1H, d, J=2.4Hz), 10.99(1H, s), 13.55 (1H, brs)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-bromo-2-chloro-3-methoxybenzoate, its application will become more common.

Reference:
Patent; Japan Tobacco Inc.; EP1564210; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 61500-87-6, name is Methyl 2-amino-4-(trifluoromethyl)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. Safety of Methyl 2-amino-4-(trifluoromethyl)benzoate

Step 2: methyl 2-(acetylamino)-4-(trifluoromethyl)benzoate To a solution of the product from Step 1 (5.34 g) in dioxane (25 ml) was added acetic anhydride (6 ml) and pyridine (4 ml). After 60 hours of stirring at 80C, the solution was concentrated under reduced pressure and the residue was dissolved into ethyl acetate. The organic layer was washed with 2M sodium carbonate, 10% aqueous HCl, water and brine, dried over sodium sulfate and evaporated. The product was purified by flash chromatography (ISCO, 5%-20% ethyl acetate in hexanes) to provide a beige solid (5.27 g). LRMS (ES+) m/z 262.0 (M+H)+.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.R.L.; RUDD, Michael, T.; MCCAULEY, John; LIVERTON, Nigel; GRISE-BARD, Christiane; BROUCHU, Marie-Christine; CHARRON, Sylvie; AULAKH, Virender; BACHAND, Benoit; BEAULIEU, Patrick; ZAGHDANE, Helmi; HAN, Yongxin; FERRARA, Marco; HARPER, Steven; SUMMA, Vincenzo; CHACKALAMANNIL, Samuel; VENKATRAMAN, Srikanth; SHAH, Unmesh; VELAZQUEZ, Francisco; WO2013/74386; (2013); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 167760-75-0, These common heterocyclic compound, 167760-75-0, name is Methyl 4-amino-3-(trifluoromethyl)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.

6.54 g (30 mmol) methyl 4-amino-3-trifluoromethyl-benzoate are suspended in 50 ml 32% hydrochloric acid and cooled to -20 C. A solution of 2.28 g (33 mmol) sodium nitrite in 20 ml of water is added dropwise. The mixture is stirred for 3 hours at -20 to -10 C., then 27.08 g (120 mmol) tin-(II)-chloride dihydrate in 30 ml hydrochloric acid are added dropwise within 0.25 hours. The reaction mixture is stirred for 2 hours at -10 C., then acidified with cooling. The suspension is suction filtered through kieselguhr and washed with chloroform. The phases of the filtrate are separated, the aqueous phase is extracted with chloroform. The combined organic phases are dried and evaporated to dryness. The residue is precipitated as the hydrochloride, then stirred with diethyl ether. Yield: 4.02 g (50% of theoretical)

Statistics shows that Methyl 4-amino-3-(trifluoromethyl)benzoate is playing an increasingly important role. we look forward to future research findings about 167760-75-0.

Reference:
Patent; Breitfelder, Steffen; Maier, Udo; Hoenke, Christoph; Joergensen, Anne T.; Pautsch, Alexander; Brandl, Trixi; Grauert, Matthias; Hoffmann, Matthias; Scheuerer, Stefan; Erb, Klaus; Pieper, Michael; Pragst, Ingo; US2007/238730; (2007); 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. 146307-51-9, name is trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

To a solution of (frans)-methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate (Intermediate 18A) (1 .5 g, 5.8 mmol) in EtOH (24 mL) and THF (2.7 mL), cooled on ice, was added calcium chloride (1 .29 g, 1 1 .7 mmol) portion wise to give a milky suspension. NaBH4 (882 mg, 23.3 mmol) was then added portion wise over ca. 25 min and the reaction was stirred on ice for 1 h. The bath was removed and the mixture was allowed to stir at room temperature overnight. The reaction was cooled to 10 C and to this was added 5% aqueous K2CO3 (5.4 mL) dropwise, to give a pH of ca. 1 1 . A white precipitate formed and was isolated by filtration. The solid was stirred with EtOAc (50 mL) and water (14 mL). The layers were separated and the organic layer was washed with 0.5 M aqueous HCI (5 mL), water and brine, dried over MgS04, filtered, and concentrated to give the title compound (474 mg) as a white solid. The initial filtrate was concentrated, then dilute with saturated aqueous NH4CI and extracted with EtOAc (3X). Combined organics were washed with brine and dried over Na2SC>4, filtered, and concentrated to give the title compound (724 mg) as a white solid. Total isolated product was 1 .1 9 g (89% yield). 1H NMR (400 MHz, CD3SOCD3) delta 0.78-0.93 (m, 2 H), 1 .01 -1 .15 (m, 2 H), 1 .35 (s, 9 H), 1 .64-1 .80 (m, 4 H), 3.10 (d, J = 8 Hz, 1 H), 3.16 (t, J = 6 Hz, 2 H), 4.33 (t, J = 5 Hz, 1 H), 6.64 (d, J = 8 Hz, 1 H).

According to the analysis of related databases, 146307-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics