Tag: M.W=100-200

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. 172217-11-7, name is Ethyl 2-amino-6-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Ethyl 2-amino-6-chlorobenzoate

A solution of sodium nitrite (4.5 g) in water (100 ml) was added dropwise during 5 minutes to a stirred suspension of ethyl 6-chloroanthranilate (12.7 g) in a mixture of concentrated sulphuric acid (27.9 ml), water (38 ml) and ice (76 g). The reaction mixture was stirred at 0C for an additional 20 minutes and then heated to 120C for 1 hour. The resultant mixture was poured into a mixture of ice and water and the product was extracted with diethyl ether. The organic phase was washed in turn with water and brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a 4:1 mixture of petroleum ether (b.p. 60-80C) and methylene chloride as eluent. There was thus obtained ethyl 6-chloro-2-hydroxybenzoate (9.8 g); NMR Spectrum : (DMSOd6) 1.3 (t, 3H), 4.3 (q, 2H), 6.9 (d, 1H), 6.95 (d, 1H), 7.25 (d, 1H), 10.45 (br s, 1H).

The synthetic route of 172217-11-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; EP1292594; (2004); B1;,
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Electric Literature of 5445-17-0, 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. 5445-17-0, name is Methyl 2-bromopropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

methanol (10 mL) was added to a 100 mL flask containing magnetite, and aniline (1.82 mL, 20 mmol), sodium acetate (1.8 g, 22 mmol) and methyl 2-bromopropionate (2.45 mL) were added successively under stirring., 22 mmol), refluxed at 80C for 18 hours.After completion of the reaction, 100g to 200 mesh silica gel 1g was added to the mixture, the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography (n-hexane/ethyl acetate 50 to 30:1) to give 3.5 g of a colorless oily intermediate.The yield is 98%;

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

Reference:
Patent; Henan University; Jiang Zhiyong; Shao Tianju; Zhao Xiaowei; Liu Yang; Qiao Baokun; (9 pag.)CN108017580; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 1459-93-4, name is Dimethyl isophthalate, 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 1459-93-4, name: Dimethyl isophthalate

6.0 kg of dimethyl isophthalate, 21.0 kg of 2,2,6,6-tetramethyl-4-aminopiperidine was added to a 50 liter reactorIn the reactor all the materials off the entrance. The reaction was carried out at 190 C for 2 hours and then at 230 C for 5 hours. The temperature was lowered to below 180 C, and excess 2,2,6,6-tetramethyl-4-aminopiperidine was recovered by vacuum distillation under a vacuum pump. Then use water to generateN, N’-bis (2,2,6,6-tetramethyl-4-piperidinyl) -1,3-benzenedicarboxamide, filtered and dried to give 12.8 kg of acicular white crystalline product , Yield 93.5%.

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 isophthalate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xiangtan University; Luo Zhiqiang; Zhang Lingjun; Zhang Jing; Ji Yongsheng; Ji Changfu; Zeng Yang; Liu Mengyan; Zhou Ji; Liu Minna; Wang Zhe; (7 pag.)CN106905225; (2017); A;,
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Synthetic Route of 105-53-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 105-53-3 name is Diethyl malonate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a suspension of sodium hydride (900 mg, 37.5 mmol) indry THF (30 mL), diethyl malonate 6a (2 g, 12.5 mmol) was added and the reaction mixturewas stirred at r.t. for 10 min. Later, allyl bromide (1.30 mL, 14.80 mmol) was added and thestirring was continued for 12 h at same temperature. At the conclusion of the reaction (TLCmonitoring), the reaction mixture was diluted with EtOAc and the aqueous layer wasextracted with CH2Cl2. Then, the solvent was removed under reduced pressure and the crudeproduct was purified by silica gel column chromatography (2% EtOAc-petroleum ether) toafford the mono-allylated compound 13a as a thick colourless liquid (1.52 g, 63%) along withdi-allylated compound 14a as a thick colourless liquid (693 mg, 24%). The 1H and 13C NMRspectra matched with the literature reported spectral data.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl malonate, and friends who are interested can also refer to it.

Reference:
Article; Kotha, Sambasivarao; Ali, Rashid; Tiwari, Arti; Synthesis; vol. 46; 18; (2014); p. 2471 – 2480;,
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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. 57625-74-8, name is Methyl 2-methyl-2-phenylpropanoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C11H14O2

Example-l: Preparation of 2-methyl-2-phenylpropanoic acid (FormuIa-3) Methyl 2-methyl-2-phenylpropanoate compound of formula-2 (100 gm) and methanol (500 ml) were added to a pre-cooled mixture of sodium hydroxide (45 gm) and water (500 ml) at 10-15C. Heated the reaction mixture to reflux temperature and stirred for 3 hrs at the same temperature. Distilled off the solvent completely from the reaction mixture under reduced pressure and cooled the reaction mixture to 25-30C. Water was added to the reaction mixture and cooled to 5-10C. Acidified the reaction mixture using dil.HCl solution at 5-10C. Raised the temperature of the reaction mixture to 25-30C and stirred for 30 rhin at the same temperature. Filtered the solid, washed with water and dried the material to get the title compound. Yield: 89.0 gm.

According to the analysis of related databases, 57625-74-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; VENKAT REDDY, Ghojala; WO2014/188453; (2014); A2;,
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Reference of 924-99-2,Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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.

A solution of ethyl 3-(dimethylamino)acrylate (4.33 mL, 30.3 mmol) and triethylamine (2.446 mL, 17.55 mmol) in Et2O (46 mL) was added dropwise to a solution of (Z)-2-chloro-N-hydroxybenzimidoyl chloride (2.3 g, 12.10 mmol) in Et2O (46.0 mL) to give a white suspension which was stirred overnight at 20 C. After 19 h, the salts were filtered and then rinsed with Et2O (30 mL). The filtrate was concentrated to dryness to give 5.86 g of an orange liquid which was purified by flash chromatography using a mixture of hexane/Et2O to afford ethyl 3-(2-chlorophenyl)isoxazole-4-carboxylate 3a (2.36 g, 77% yield) as a colorless oil; 1H NMR (DMSO-d6) was consistent with the desired product; MS m/z 252.1 (MH+); HPLC 100%, Rt=1.96 min, column 2.

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-(dimethylamino)acrylate, its application will become more common.

Reference:
Patent; Lamarre, Daniel; US2015/133495; (2015); A1;,
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Reference of 5335-05-7, The chemical industry reduces the impact on the environment during synthesis 5335-05-7, name is Chloromethyl benzoate, I believe this compound will play a more active role in future production and life.

A similar procedure [23] and [26] to that previously described for the preparation of 2 was followed using chloromethyl benzoate (45) (106 mg, 0.76 mmol) in acetone (0.2 mL), sodium iodide (339 mg, 2.28 mmol) in acetone (2.5 mL), and the mixture stirred at room temperature for 30 min. The solvent was removed in vacuo and the residue taken up in acetonitrile (1.5 mL). A solution of 1 (200 mg, 0.38 mmol) in acetonitrile (2 mL) was added and the mixture stirred at 80 C for 16 h. The solvent was removed in vacuo with purification by flash chromatography (dichloromethane/methanol 20:1) affording 3 as a yellow solid (110 mg, 0.14 mmol, 37%). mp 165-169 C; numax(NaCl)/cm-1 1087 and 1261 (C-O ester), 1697 (CO imide), 1733 (CO ester); m/z (FAB+) 660 (M+, 100%); (Found: M+ 660.2490, C42H34N3O5 requires 660.2498).

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, Chloromethyl benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Rennison, David; Laita, Olivia; Bova, Sergio; Cavalli, Maurizio; Hopkins, Brian; Linthicum, Darwin S.; Brimble, Margaret A.; Bioorganic and Medicinal Chemistry; vol. 20; 13; (2012); p. 3997 – 4011;,
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Related Products of 42122-44-1, A common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, 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 a cooled solution (0 C, ice bath) containing 3-(3-(N-(2-(tert- butyldimethylsilyloxy)ethyl)methylsulfonamido)pyridin-4-yl)-N-(2-phenylpropan-2- yl)benzamide (0.090 g, 0.12 mmol) and dichloromethane (2 mL) was added O- (mesitylsulfonyl)hydroxylamine (0.080 g, 0.37 mmol) in dichloromethane (2 mL) quickly, dropwise. The solution was maintained at 0 C for 15 min, removed from the cooling bath and maintained at ambient temperature for 2 h. The solution was concentrated, dissolved in methanol (5 mL) and re-concentrated to afford l-amino-3- ( -(2-hydroxyethyl)methylsulfonamido)-4-(3-(2-phenylpropan-2- ylcarbamoyl)phenyl) pyridinium 2,4,6-trimethylbenzenesulfonate as a light yellow foam (470, MH+). The product thus obtained was dissolved in DMF (2.4 mL) and added slowly dropwise over 20 min to a cooled mixture (0C, ice bath) containing potassium carbonate (0.070 g, 0.50 mmol), methyl 3-(4-fluorophenyl)propiolate (0.030 g, 0.19 mmol) and DMF (2.0 mL). The mixture was kept in the cooling bath with stirring and allowed to proceed for 15 h at ambient temperature. The mixture was filtered and concentrated. Purification on silica gel (0-100% ethylacetate/hexanes, 60 min gradient) afforded methyl 2-(4-fluorophenyl)-6-( -(2- hydroxyethyl)methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl) pyrazolo[l,5-a]pyridine-3-carboxylate as a yellow residue. 1H NMR (500 MHz,CHLOROFORM-D) delta ppm 8.72 (s, 1 H), 8.24 (s, 1 H), 8.16 (s, 1 H), 7.97 – 8.00 (m, 1 H), 7.89 (t, J=7.93 Hz, 1 H), 7.77 – 7.84 (m, 2 H), 7.50 – 7.59 (m, 2 H), 7.40 – 7.49 (m, 3 H), 7.23 – 7.33 (m, 3 H), 7.12 – 7.19 (m, 3 H), 3.83 (s, 3 H), 3.62 – 3.71 (m, 1 H), 3.39 – 3.46 (m, 1 H), 3.30 – 3.39 (m, 1 H), 3.18 – 3.23 (m, 3 H), 2.63 – 2.72 (m, 1 H), 1.78 (t, J=12.21 Hz, 6 H). LCMS: retention time: 2.403 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters- Sunfire, 5u, CI 8, 4.6 x 50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3CN / 90% H20 / 10 mM TFA and solvent B was 10% H20 / 90% CH3CN / 10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 645 (MH+).

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; BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John, F.; BENDER, John, A.; BENO, Brett, R.; GRANT-YOUNG, Katharine; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle, E.; YEUNG, Kap-Sun; CHUPAK, Louis, S.; WO2011/112186; (2011); A1;,
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344-14-9, name is Dimethyl 2-fluoromalonate, 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. Computed Properties of C5H7FO4

Intermediate 345 A: Methyl 2-fluoropent-4-ynoate In a 20 mL microwave vial, a mixture of dimethyl 2-fluoromalonate (900 mg, 6.0 mmol) in DMA (5 mL) at room temperature with stirring, was treated with the slow addition of sodium hydride (240 mg, 6 mmol, 60%) at 0 C. The mixture was stirred for 10 minutes, then added 3-bromoprop-l-yne (743 mg, 5.0 mmol, 80% in xylenes) and the mixture was stirred vigorously at 25 C for 1.5 hours. TLC shows consumption of the bromide. A syringe needle was placed through the septum to allow gases to vent, then the mixture was heated at 90 C for 20 hours. The reaction was quenched with the careful addition under nitrogen of saturated NH4CI solution (0.5 mL), and extracted with ethyl acetate (3 X 25 mL). The combined extracts were dried over Na2S04 to give a few ml of a brown oil as crude product. The crude product was dissolved in ethyl acetate and rinsed 3 times with 10% LiCl to remove DMA. The organic layer was dried over sodium sulfate, and then concentrated to give an amber oil which was purified over silica gel in 9: 1 to 3 : 1 hexanes/EtOAc to afford methyl 2-fluoropent-4-ynoate (600 mg, 69% yield). NMR (400MHz, CHLOROFORM-d) delta 3.84 (s, 3H), 2.92-2.74 (m, 2H), 2.14-2.00 (m, 1H), 1.27 (d, J=5.3 Hz, 1H). LCMS 130.2 (M+H)+.

The synthetic route of 344-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GARDNER, Daniel S.; SANTELLA, Joseph B.; PAIDI, Venkatram Reddy; WU, Hong; DUNCIA, John V.; NAIR, Satheesh Kesavan; HYNES, John; (300 pag.)WO2016/210034; (2016); A1;,
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Electric Literature of 42726-73-8,Some common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, molecular formula is C8H14O4, 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.

A solution of t-butyl methyl malonate (0.69 g, 3.9 mmol) in dimethylformamide (10 mL) was treated with sodium hydride (60percent in mineral oil, 0.16 g, 3.9 mmol) at 60° C. for 30 minutes. After cooling to room temperature, a solution of the compound of Example 1(a) (1.2 g, 3.0 mmol) in dimethylformamide (10 mL) was added dropwise. After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate/hexanes (1:1, 100 mL) and washed with water (5.x.50 mL) and brine (50 mL), and dried (Na2SO4). After removing the solvent under the reduced pressure, the residue was dissolved in toluene (100 mL) and p-toluenesulfonic acid monohydrate (0.2 g, 1.0 mmol) was added. The resulting mixture was heated to reflux for 2h. After cooling to room temperature, the mixture was diluted with ethyl acetate (50 mL), washed with saturated NaHCO3 (50 mL) and brine (50 mL), and dried (Na2So4). After removing the solvent under the reduced pressure, the residue was purified by flash column chromatography (silica gel, 1:4 EtOAc/hexanes) to afford 0.47 g (40percent) of the title compound as a brown oil: 1H NMR (CDCl3) delta 7.34 (m, 5H), 4.55 (s, 2H), 3.67 (s, 3H), 3.54 (m, 3H), 3.33 (m, 2H), 3.05 (m, 1H), 2.68 (m, 3H), 2.16 (m, 1H), 1.25-1.70 (m, 12H), 0.93 (t, 3H). MS(ES) m/e 390 [M+H]+.

The synthetic route of 42726-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xiang, Jia-Ning; Christensen IV, Siegfried B.; Liao, Xiangmin; Cummings, Maxwell D.; US2004/77856; (2004); A1;,
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