Tag: M.W=100-200

These common heterocyclic compound, 57486-68-7, name is Methyl 2-chlorophenylacetate, 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. category: esters-buliding-blocks

EXAMPLE 35 Preparation of 1-(o-Chlorophenyl)-3-azabicyclo[3.1.0]hexane hydrochloride A stirred mixture of 36.9 g of methyl o-chlorophenylacetate, 36.0 g of N-bromosuccinimide, and 2 drops of 48% hydrobromic acid in 500 ml of carbon tetrachloride is refluxed for 20 hours and then filtered through magnesium silicate. Evaporation under reduced pressure gives methyl alpha-bromo-o-chlorophenylacetate as a straw-colored liquid.

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

Reference:
Patent; American Cyanamid Company; US4131611; (1978); A;,
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Application of 426-65-3, 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 426-65-3 as follows.

4,4,5,5,5-pentafluoro-1-phenylpentane-1,3-dione, lithium enolate salt (Scheme 1, formula 3; X=F) A solution of lithium hexamethyldisilazide in THF (1.0 M, 7.6 mL, 7.6 mmol, 1.0 eq.) was added to dry Et2O (12 mL) and cooled to -78 C. To the cooled solution was added a solution of acetophenone (0.90 g, 7.6 mmol) in Et2O (8 mL), dropwise over 15 minutes. The mixture was stirred at -78 C. for 30 minutes, then a solution of ethyl 2,2,3,3-3-pentafluoropropionate (1.26 mL, 7.95 mmol, 1.05 eq.) in Et2O (6 mL) was added in one portion. The dry ice bath was removed, and the reaction was stirred, warming to room temperature, for 1 hour. The reaction was then evaporated to yield a tacky solid which was triturated with hexane repeatedly to yield 2.04 g (99%) of 3 as a pink solid: Rf 0.38 (50% EtOA/hexanes): 1H NMR (DMSO-d6) S 7.96 (d, 2H), 7.64 (t, 1H), 7.52 (dt, 2H), 6.64 (s, 1H).

According to the analysis of related databases, 426-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MICROBIOTIX, INC.; Basu, Arnab; Mills, Debra M.; Peet, Norton P.; Williams, John D.; US9101635; (2015); B2;,
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Related Products of 27741-65-7, The chemical industry reduces the impact on the environment during synthesis 27741-65-7, name is Ethyl 2-cyclobutylideneacetate, I believe this compound will play a more active role in future production and life.

[00269] Step 1 : Ethyl 2-cyclobutylideneacetate (408.9 mg, 2.917 mmol) was dissolved in THF (14.6 mL, 0.2 M). The solution was degassed with N2, and treated with copper (I) iodide (61 1.1 mg, 3.209 mmol). This was cooled to 0 C and treated with chlorotrimethylsilane (405.8 mu, 3.209 mmol). The mixture was stirred at 0 C for 10 minutes and then treated with ethylmagnesium bromide (2917 mu, 2.917 mmol). This was stirred at 0 C for 1 hour. The mixture was quenched with water, and the organics were extracted with Et20 twice, washed with brine and dried with Na2S04. This was then concentrated down to give ethyl 2-(l-ethylcyclobutyl)acetate (0.2675 g, 53.8%).

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-cyclobutylideneacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James, F.; COOK, Adam; GAUDINO, John; GUNAWARDANA, Indrani, W.; HICKEN, Erik, James; HUNT, Kevin, W.; LYON, Michael; METCALF, Andrew, T.; MOHR, Peter, J.; MORENO, David, A.; NEWHOUSE, Brad; REN, Li; SCHWARZ, Jacob; CHEN, Huifen; GAZZARD, Lewis; SCHMIDT, Jane; DO, Steve; WO2015/103137; (2015); 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. 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 294190-18-4

[01713] Step 1 : Synthesis of methyl 5-chloro-3-(isobutyl amino)-2-methylbenzoate[01714] To a stirred solution of methyl 3-amino-5-chloro-2-methyl benzoate (5.0 g, 25 mmol) and isobutyraldehyde (4.5 g, 62 mmol) in methanol (50 mL), acetic acid (3.0 g, 50 mmol) was added and reaction stirred at room temperature for 2 h. Then sodium cyanoborohydride (3.94 g, 62 mmol) was added at 0C and reaction stirred overnight at room temperature. On completion, the solvent was removed under reduced pressure and the crude material was purified by column chromatography to afford the title compound (6.0 g, 94 %).

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; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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These common heterocyclic compound, 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-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. HPLC of Formula: C6H9ClO3

A) 1-(3-Iodophenyl)-4-methoxy-1H-pyrrole-2(5H)-one To a mixture of 3-iodoaniline (5.32 g) and tetrabutylammonium iodide (0.897 g) in acetonitrile (20 mL) was added a mixture of methyl 4-chloro-3-methoxy-2-(E)-butenoate (4.13 mL) and acetonitrile (20 mL). To the reaction mixture was added a mixture of triethylamine (3.72 mL) and acetonitrile (10 mL). The reaction mixture was stirred overnight at 50 C. To the reaction mixture were added methyl 4-chloro-3-methoxy-2-(E)-butenoate (1.65 mL) and triethylamine (1.69 mL). The reaction mixture was stirred at 50 C. for 5 hr and cooled to room temperature. The reaction mixture was adjusted to pH 3 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. To the residue were added toluene (40 mL) and acetic acid (1.0 mL) at room temperature. The reaction mixture was heated at 50 C. for 1.5 hr. The reaction mixture was concentrated under reduced pressure and crystallized from methanol/diisopropylether to give the title compound (3.41 g). MS: [M+H]+ 316.0.

The synthetic route of (E)-Methyl 4-chloro-3-methoxybut-2-enoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOIKE, Tatsuki; FUSHIMI, Makoto; AIDA, Jumpei; IKEDA, Shuhei; KUSUMOTO, Tomokazu; SUGIYAMA, Hideyuki; TOKUHARA, Hidekazu; (170 pag.)US2016/318864; (2016); A1;,
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Related Products of 2065-23-8, These common heterocyclic compound, 2065-23-8, name is Methyl 2-phenoxyacetate, 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 methyl phenoxyacetate obtained by distillation, 1.72 g of tin tetrachloride having a purity of 99% and 0.60 g of 2,5-dichlorothiazole having a purity of 99% were added.279.41 g of 99% pure sulfuryl chloride was added at 60 C to react.After the addition, the reaction was kept at this temperature for 0.5 h.Distilling at a pressure of 1 kPa and collecting fractions at 115-125 C,234.12 g of methyl 2,4-dichlorophenoxyacetate was obtained, and the content was 99.18%.

Statistics shows that Methyl 2-phenoxyacetate is playing an increasingly important role. we look forward to future research findings about 2065-23-8.

Reference:
Patent; Shandong Runbo Biological Technology Co., Ltd.; Sun Guoqing; Hou Yongsheng; Chi Zhilong; Zhang Liguo; Hu Yishan; (15 pag.)CN108947822; (2018); A;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, 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 924-99-2, name: Ethyl 3-(dimethylamino)acrylate

95 mg (0.27 mmol) of 2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoic acid were boiled with 0.98 ml of thionyl chloride under reflux for 3 hours. The thionyl chloride was distilled off, and the residue was mixed with 3 ml of toluene and concentrated in vacuo. The residue was taken up in 2 ml of toluene and added to a solution of 39 mg (0.27 mmol) of ethyl 3-dimethylaminoacrylate, 6 mul of triethylamine and 1 ml of toluene. The mixture was heated at 90 C. for 3 hours. The mixture was concentrated and chromatographed on silica gel (heptane:ethyl acetate=75:25 to 0:100 in 45 minutes). 30 mg (23%) of the desired product were obtained. MS: M+H=477/479

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-(dimethylamino)acrylate, and friends who are interested can also refer to it.

Reference:
Patent; Aventis Pharma Deutschland GmbH; US2005/182085; (2005); 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of trans-Ethyl 4-hydroxycyclohexanecarboxylate

Intermediate 30: m-Ethyl 4-[[2-[5-[(2,4<5-trifluorophenvDapi-ino]-1.3,4-oxadiazol-2- yll -3H-benzoimidazol-5-yll oxyl cyclohexane-l-carboxylate; i) Ethyl 4-(4-amino-3-nitro-phenoxy)cvclohexane-l-earboxylate; Diisopropyl azodicarboxylate (1.72 mL, 8.71 mmol) was added in one portion to a stirred solution of ethyl 4-hydroxycyclohexanecarboxylate (1.0 g, 5.8 mmol), 4-amino-3- nitrophenol (2.69 g, 17.4 mmol) and triphenylphoshine (2.29 g, 8.71 mmol) in THF (40 mL) under an argon atmosphere. The reaction mixture was stirred at ambient temperature for 16 h and then EtOAc (150 mL) and water (150 niL) were added. The layers were separated and the organic layer was washed with a IM aqueous solution of HCl (150 mL), then a IM aqueous solution of sodium hydroxide (150 mL) and then brine (150 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to leave a dark brown solid. This solid was purified by column chromatography, eluting with a gradient of 30 to 40percent EtOAc in isohexane, to give the title compound as an impure orange oil (1.15 g, 64percent), that was used with no further purification; MS m/e MH+ 474.

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/141517; (2007); 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. 5445-17-0, name is Methyl 2-bromopropanoate, A new synthetic method of this compound is introduced below., Computed Properties of C4H7BrO2

2.50 g (9.05 mmol) of tert-butyl 2-[(benzylamino)methyl]azetidine-1-carboxylate [racemate] were dissolved in dichloromethane (150 ml), 5.55 ml (4.03 g, 39.8 mmol) of triethylamine and 3.04 ml (4.53 g, 27.1 mmol) of methyl 2-bromopropanoate [racemate] were added and the mixture was stirred at RT overnight. 5.55 ml (4.03 g, 39.8 mmol) of triethylamine and 3.04 ml (4.53 g, 27.1 mmol) of methyl 2-bromopropanoate [racemate] were added, and the mixture was stirred at 40° C. overnight. A further 5.55 ml (4.03 g, 39.8 mmol) of triethylamine and 3.04 ml (4.53 g, 27.1 mmol) of methyl 2-bromopropanoate [racemate] were then added, and the mixture was stirred at 40° C. overnight. After cooling to room temperature, the mixture was diluted with water and dichloromethane, and the phases were separated. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and then freed of the solvent under reduced pressure. The crude product obtained was purified by silica gel chromatography (dichloromethane, then dichloromethane/methanol=100:1). Yield: 3.22 g (94% of theory).

The synthetic route of 5445-17-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; Allerheiligen, Sven; Buh, Mueller Anya; Engel, Karen; Gardez, Hirishtof; Garike, kristen Mathias; Gerrish, Mihael; Hite, Meyer Stefan; Heels, Alexander; Kinjel, Tom; Lina, Wu Phillip; Riddle, Bernd; Rurik, Susanne; Schmidt, Martina Victoria; Strasse, Burgeo Julia; Tersteegen, Adrian; (113 pag.)KR2016/16815; (2016); A;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 94994-15-7, name is Methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylate, 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 94994-15-7, Formula: C11H18O3

Under a nitrogen atmosphere, 4.7 g of the compound represented by the formula (I-70-3), 2.5 g of pyridine and 50 mL of dichloromethane were added to the reaction vessel. 3.0 g of methanesulfonyl chloride was added dropwise while cooling with ice, and the mixture was stirred at room temperature for 3 hours. It was poured into water and washed sequentially with 5% hydrochloric acid and brine. Purification by column chromatography (silica gel, hexane / ethyl acetate) gave 5.9 g of a compound represented by the formula (I-70-4).

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-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DIC CORPORATION; HORIGUCHI, MASAHIRO; AOKI, YOSHIO; HAYASHI, TAKUO; (66 pag.)JP2017/210409; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics