Tag: M.W=100-200

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. 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Step B; 2,5-Dimethyl-4-thiocyanato-phenol 30 (5.75 g, 32.1 mmol) is dissolved in acetonitrile (25 mL). Powdered cesium carbonate (15.32 g, 47.0 mmol) is added. Then 2- bromo-2-methyl-propionic acid methyl ester (4.50 mL, 34.8 mmol) is added and the mixture is stirred at 6O0C for 18 h. Filtration and concentration, followed by silica gel chromatography (0-50% ethyl acetate in hexanes) yielded 2-(2,5-dimethyl-4-thiocyanato- phenoxy)-2-methyl-propionic acid methyl ester 31 (3.88 g, 43%) as an oil: 1H-NMR (400 MHz, CDCl3) (rotamers are present; the data given is for the most abundant isomer) delta = 7.39 (s, IH), 6.50 (s, IH), 3.78 (s, 3H), 2.42 (s, 3H), 2.20 (s, 3H), 1.62 (s, 6H). MS calcd. for C14HnNNaO3S (M+Na+) 302.1, found 302.1.

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; IRM LLC; WO2007/56496; (2007); A1;,
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These common heterocyclic compound, 36692-49-6, name is Methyl 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. HPLC of Formula: C8H10N2O2

Example 101; (2Z,5Z)-2-[(2,6-dichlorophenyl)imino]-5-{[2-(2-pyridinyl)-1H-benzimidazol-6-yl]m ethylidene}-1,3-thiazolidin-4-one; (a) methyl 2- (2-pyridinyD-lHbenzimidazole-5-carboxylate; A solution of 2-pyridinecarbaldehyde (0.19 g, 1.80 mmol) in 40 % aq. sodium hydrogen sulfite was stirred for 1 h at room temperature before being added to a solution of methyl 3,4-diaminobenzoate (0.300 g, 1.80 mmol) in ethanol (3 mL). The resulting mixture was stirred under reflux overnight. Then it was taken in 10 mL of water and extracted with 3 x 10 mL of ethyl acetate, dried over magnesium sulfate, filtrated and concentrated. Flash chromatography (silica gel, 10 % methanol, dichloromethane) afforded the desired compound as white powder in very low yield (13 %) [MS (ES+) m/e 254 [M+H] +].

The synthetic route of Methyl 3,4-diaminobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/82901; (2005); A1;,
Ester – Wikipedia,
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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 3377-20-6 as follows. Safety of Diethyl 2-methylenemalonate

nBuLi solution (2.5 M in hexanes, 1.4 mL, 3.6 mmol) was added, dropwise over 2 min., to a cooled (dry ice/acetone/ethylene glycol bath at -20 C) solution of N,N,N?-trimethylethylenediamine (388 mg,3.80 mmol) in THF (4.0 mL). After stirring for 15 min., a solution of 4- chlorobenzaldehyde (486 mg, 3.45 mmol) in THF (3.0 mL) was added dropwise over 4 min. Additional THF (2×1.0 mL) was used to complete the transfer. After 15 min., more nBuLi solution (2.5 M in hexanes, 4.3 mL, 11 mmol) was added, dropwise over 4 min. After stirring at this temperature for 2.8 h, the reaction mixture was cooled in a dry ice/acetone bath. After stirring for 10 min., diethyl ketomalonate (2.3 mL, 15 mmol) was added to the reaction mixture, dropwise over 5 min. After 5 min., the reaction was quenched by rapid addition of aq. HCl (1.0 M, excess), and cooling was ended. The resulting mixture was extracted with dichloromethane (3x), and the combined organic layers were dried (sodium sulfate) and evaporated to afford a clear, amber oil (3.30 g) that darkened over time. Repeated chromatographic purification (160 g silica gel, 1:9 to 3:7 EtOAc/heptane gradient followed by 44 g silica gel, 1:9 dichloromethane/heptane to dichloromethane to 1:19 EtOAc/dichloromethane gradient) afforded the title compound as a clear, colorless oil (234 mg, 22 % yield). LCMS (ESI) m/z: 337.2 [M+Na] (42 %). 1H NMR (400 MHz, CDCl3) delta 1.30 (t, J = 7.1 Hz, 3H), 1.33 (t, J = 7.1 Hz, 3H), 2.70 (d, J = 7.6 Hz, 1H), 4.25 (dq, J = 10.8, 7.1, 1H), 4.32 (dq, J = 10.8, 7.1, 1H), 4.33 (dq, J = 10.8, 7.1, 1H), 4.37 (dq, J = 10.8, 7.1, 1H), 5.87 (dt, J = 7.7, 0.6 Hz, 1H), 6.99-7.03 (m, 2H), 7.29-7.35 (m, 1H).

According to the analysis of related databases, 3377-20-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rocke, Benjamin N.; Conn, Edward L.; Eisenbeis, Shane A.; Ruggeri, Roger B.; Tetrahedron Letters; vol. 53; 41; (2012); p. 5467 – 5470;,
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Synthetic Route of 2905-65-9,Some common heterocyclic compound, 2905-65-9, name is Methyl 3-chlorobenzoate, molecular formula is C8H7ClO2, 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: The following experimental procedure for the partial reduction of ethyl benzoate to benzaldehyde is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with ethyl benzoate (0.07 mL, 0.5 mmol) and THF (5 mL). After cooling to 0 C, cis-2,6-dimethylmorpholine-modified Red-Al (2.5 mL, 0.4 M 1.0 mmol) was added dropwise and the mixture was stirred for 30 min at the room temperature. The reaction was stopped aqueous 1 N HCl (5 mL) and the product was extracted with diethyl ether (10 mL). The ether layer was dried over anhydrous magnesium sulfate. GC analysis showed a 98% yield of benzaldehyde. All products in Table 1 were confirmed through comparison with GC data of authentic sample.

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

Reference:
Article; Shin, Won Kyu; Kang, Daehoon; An, Duk Keun; Bulletin of the Korean Chemical Society; vol. 35; 7; (2014); p. 2169 – 2171;,
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Adding a certain compound to certain chemical reactions, such as: 13195-64-7, name is Diisopropyl malonate, 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 13195-64-7, SDS of cas: 13195-64-7

To a stirred suspension of NaH (11.7 g, 293 mmol, 60percent purity) in DMF (100 ml) was added diisopropylmalonic ester dropwise, keeping the temperature below 40 0C. The resulting mixture was stirred for 1 h at RT and then l,3-dibromo-2,2-dimethoxypropane (34.8 g, 133 mmol) was added in one portion. The resulting mixture was heated at 140 0C for 24 h and then cooled to RT. Saturated NH4Cl aqueous (400 ml) was added and the mixture extracted with hexane (2 x 190 ml). The combined organic phases were washed with H2O (2 x 250 ml) saturated NaHCO3 (2 x 250 ml), H2O (2 x 250 ml) and brine (250 ml). The organic phase was dried (Na2SO4), filtered and concentrated at reduced pressure to provide an orange oil. Purification by in vacuo distillation to remove excess of l,3-dibromo-2,2-dimethoxypropane (b.p. 60-62 0C, 0.1 mniHg) and diisopropylmalonic ester (b.p 78-80 0C, 0.1 mmHg) provided the title compound (20 g, 52percent) as orange oil in the distillation flask. MS data: Calculated MH+ (289); Found 100percent (MH+) m/z 289.NMR data: 1H NMR (360 MHz, CHLOROFORM- d) delta ppm 5.07 (2 H, spt, J=6.3 Hz), 3.16 (6 H, s), 2.70 (4 H, s), 1.24 (12 H, d, J=6.4 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, Diisopropyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; WO2009/135842; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 2216-92-4, These common heterocyclic compound, 2216-92-4, name is N-Phenylglycine Ethyl Ester, 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 1 Preparation of N-(1-oxo-9Z-octadecenyl)-N-phenylglycine, ethyl ester STR3 Oleoyl chloride (0.01 mole), N-phenylglycine ethyl ester (0.01 mole) and triethylamine (1.4 ml) in tetrahydrofuran (100 ml) was stirred overnight at room temperature. The solvent was removed by rotary evaporator and the residue was dissolved in ethyl acetate (50 ml) and washed with water (50 ml). The ethyl acetate solution was dried over sodium sulfate, filtered and the solvent removed by a nitrogen stream to give an oil which was purified by chromatography on silica gel to give the title compound. Analysis calcd. for C28 H45 NO3 (443.65): C, 75.80; H, 10.22; N, 3.16. C, 75.51; H, 10.32; N, 2.94.

The synthetic route of 2216-92-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G. D. Searle & Co.; US4551279; (1985); A;,
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Synthetic Route of 40872-87-5, The chemical industry reduces the impact on the environment during synthesis 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, I believe this compound will play a more active role in future production and life.

In one example of the inventive process, the reaction was conducted with methyl 3-amino-4-chloro-benzoate and 1-cyclopentyl-2-pyridinyl acetylene as the starting materials (Scheme 7). Suitable choices of ligand, base and solvent was important for obtaining satisfactory results as shown in Table 1. Several ligands were examined. It was found that the reaction proceeded smoothly to afford the desired indole product when using either ligand 4a, 4b or 5 in the presence of n-Bu4N+OAc-. The major side-reaction was homocoupling of the arylchloride via double amination (entries 1-3). The proper choice of base, solvent, temperature, and concentration was important to minimize the formation of the amination byproduct and also maximize the desired regioselectivity. By using inorganic bases such as K2CO3, a cleaner reaction could be obtained than by using n-Bu4N+OAc- as base. When a ferrocene ligand such as bis(diisopropylphosphino)ferrocene was employed, in combination with K2CO3 as base, the indolization of 2-chloroaniline with the internal acetylene completed rapidly, providing the product in high purity and regioselectivity (entry 4). Addition of LiCl or LiI as additive did not improve the yield. Instead, it slowed down the reaction (entries 5-6). With reduced catalyst loading (5 mol %), the reaction also proceeded smoothly and cleanly (entry 7). Changing the ratio of ligand to palladium acetate from 2:1 to 1:1 prolonged the reaction time (entry 8). Using K2CO3 as base, ligands 4a, 4b or 6 also afforded good results (entries 9-10). The wavelength used was 240 nm. TABLE I Base Time Entry (Scale) (eq) Catalyst (h) Result* 1 (100 mg) n-Pd(OAc)2 (10%) 4 Complete conversion of Bu4N+OAc- 2-(Di-t- starting material, giving 45 (2.5 eq) butylphosphino)- area % product and 33 biphenyl (40%) area % byproduct. 2 (100 mg) n-Pd(OAc)2 (10%) 3 Ratio of the desired product Bu4N+OAc- 1,1′- to starting material (2.5 eq) Bis(diphenylphosphino) (cholroaniline) was 5:1, ferrocene(20%) about 35 area % unknown impurities. The ratio of the regioisomers was 9:1. 3 (200 mg) n-Pd(OAc)2 (10%) 14 Complete conversion of the Bu4N+OAc- 1,1′-Bis(di-i- starting material, about 35 (2.5 eq) propylphosphino) area % of unknown ferrocene(20%) impurities. The ratio of the regioisomers was 9:1. 28% isolated yield was obtained through column chromatography for two steps. 4 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 3 Complete conversion of the 1,1′-Bis(di-i- starting material. The propylphosphino) desired product was formed ferrocene(20%) in 88 area % purity. The ratio of the regioisomers was 20:1. 5 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 Ratio of the desired product 1,1′-Bis(di-i- to the starting material was LiCl (1 eq) propylphosphino) 14:1. The ratio of the ferrocene(20%) regioisomers was 19:1. 6 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 The ratio of the desired 1,1′-Bis(di-i- product to the starting LiI (1 eq) propylphosphino) material was 1.6:1. ferrocene(20%) 7 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 5:1. The ratio ferrocene(10%) of regioisomers was 18:1. 8 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 2.5:1. The ferrocene(6%) ratio of regioisomers was 19:1. 9 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 Complete conversion of the 2-(Di-t- starting material, with about butylphosphino)- 20 area % impurities. The biphenyl (10%) ratio of the regioisomers was 20:1. 10 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired Tricyclohexylphosphine product to the starting (10%) material was 4:1. Ratio of the regioisomers was 18:1. *Ratios of product were measured by HPLC analysis

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 3-amino-4-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 82782-85-2, These common heterocyclic compound, 82782-85-2, name is Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, 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: A solution of pyrrole 1 (0.20 g, 1.10 mmol) in anhydrous THF (2 ml) was added to a stirred suspension of NaH (55.0 mg, 2.29 mmol) (pre-rinsed with anhydrous hexane from a 55% dispersion in mineral oil) in anhydrous THF (10 ml) under an argon atmosphere, and the mixture was stirred for 30 min. Then a solution of iodomethane (0.14 ml, 2.19 mmol) in THF (5 ml) was added dropwise, and the mixture was stirred at 40C until the starting pyrrole was consumed (TLC control). The mixture was cooled and quenched with saturated NH4Cl solution, the product was extracted with CH2Cl2 (3×20 ml). The solvent was evaporated, the residue was purified by column chromatography on SiO2 (light petroleum-ethyl acetate, 5:1.

Statistics shows that Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 82782-85-2.

Reference:
Article; Torosyan, Seda A.; Zagitov, Vadim V.; Gimalova, Fanuza A.; Biglova, Raisa Z.; Miftakhov, Mansur S.; Mendeleev Communications; vol. 28; 2; (2018); p. 192 – 194;,
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Reference of 57486-68-7,Some common heterocyclic compound, 57486-68-7, name is Methyl 2-chlorophenylacetate, molecular formula is C9H9ClO2, 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 a stirred solution of the Methyl 2-chlorophenylacetate (0,86 ml; 5,31 mmol) in dichloromethane (10,2 ml; 159 mmol) are added N- bromosuccinimide (1.04 g; 5.84 mmol) and azobisisobutyronitrile (43,6 mg; 0,27 mmol) at room temperature and the mixture is stirred at 100 C for 16 h under argon atmosphere. The reaction mixture is cooled down to room temperature. The mixture is diluted with diethyl ether and filtered. The filtrate is evaporated to dryness. The oily residue containing solid succinimid is diluted with heptane and filtered again. The solvent is removed to afford Bromo-(2-chloro-phenyl)-acetic acid methyl ester (1.38 g; 4.56 mmol; 86 % of theory). 1H NMR (500 MHz, Chloroform-d) delta 7.69 (dd, J = 7.6, 1.8 Hz, 1H), 7.31 (dd, J = 7.6, 1.7 Hz, 1H), 7.24 (td, J = 7.6, 1.7 Hz, 1H), 7.21 (dd, J = 7.5, 1.8 Hz, 1H), 5.84 (s, 1H), 3.74 (s, 3H).

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

Reference:
Patent; MERCK PATENT GMBH; DOBELMANN-MARA, Lars; RIEDMUELLER, Stefan; SCHRAUB, Martin; (166 pag.)WO2018/149853; (2018); A1;,
Ester – Wikipedia,
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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. 110-42-9, name is Methyl decanoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl decanoate

EXAMPLE 8 14.8 g (0.083 mole) of triethylene glycol monoethyl ether was added dropwise to a mixture consisting of 1.6 g (0.042 mole) of sodium borohydride, 10 ml of xylene and 5 g (0.027 mole) of methyl caprate at 95 C. over two hours while agitating the mixture. Subsequently, the mixture was agitated at the same temperature for 1.5 hours. After cooling to room temperature, the mixture was neutralized with dilute sulfuric acid. As a result, n-decanol was obtained in 99% yield.

According to the analysis of related databases, 110-42-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kao Corporation; US5196601; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics