Tag: M.W=100-200

Reference of 89-91-8, These common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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 mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

Statistics shows that Methyl 2,2-dimethoxyacetate is playing an increasingly important role. we look forward to future research findings about 89-91-8.

Reference:
Article; Adib, Mehdi; Saeedi, Sara; Soheilizad, Mehdi; Bayanati, Maryam; Tajbakhsh, Mahmood; Amanlou, Massoud; Journal of Chemical Research; vol. 40; 5; (2016); p. 314 – 317;,
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Related Products of 15441-07-3,Some common heterocyclic compound, 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, molecular formula is C4H7ClO4S, 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 14 N-isobutyl-3-amidosulfopropionic Acid To 14.6 parts of isobutylamine and 100 parts of water there are added dropwise at 0 C, with stirring 18.65 parts of methyl 3-chlorosulfonylpropionate and then simultaneously from separate dropping funnels 18.65 parts of methyl 3-chlorosulfonylpropionate and 54 parts of 14.8% caustic soda solution. Stirring is continued for a further hour at 0 C and 4 hours at room temperature; 8.8 parts of sodium hydroxide are added and the mixture is heated at 60 C for 4 hours. The reaction mixture is acidified with a 2N H2 SO4 solution to a pH of 1 and the resulting precipitate is filtered off, washed with 100 parts of water and dried at 40 C/25 mm. Yield: 24.6 parts (59% of theory) of white crystalline N-isobutyl-3-amidosulfopropionic acid, m.p. 132-134 C (after recrystallization from H2 O).

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-(chlorosulfonyl)propanoate, its application will become more common.

Reference:
Patent; BASF Aktiengesellschaft; US4060522; (1977); A;,
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Adding a certain compound to certain chemical reactions, such as: 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, 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 18595-12-5, HPLC of Formula: C9H11NO2

Methyl 5-amino-2-methylbenzoate (1.0 eq, 3.75 g) was dissolved in acetic acid (70 ml). N-Iodosuccinimide (1.0 eq, 5.27 g) was added portionwise over 60 minutes. The mixture was stirred at room temperature for 30 minutes. Acetic acid was evaporated. The residue was diluted with ethyl acetate (80 ml) and neutralized with saturated sodium carbonate (80 ml). The organic layer was washed with 1M sodium thiosulfate (2¡Á40 ml), then water (2¡Á40 ml) and brine (2¡Á40 ml). The material was purified by flash chromatography on silica gel (gradient 10% to 30% ethyl acetate in hexanes) to provide methyl 5-amino-4-iodo-2-methylbenzoate as a yellow-orange solid (3.19 g, 49% yield). GCMS>95% pure, m/z 291. 1H NMR (400 MHz, DMSO, d6) delta 2.30 (s, 3H), 3.78 (s, 3H), 5.27 (br s, 2H), 7.24 (s, 1H), 7.54 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-amino-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; CHUA, Peter C.; Haddach, Mustapha; Nagasawa, Johnny Y.; Pierre, Fabrice; Whitten, Jeffrey P.; US2009/239859; (2009); A1;,
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Application of 431-47-0, 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 431-47-0 as follows.

Example 58 Preparation of 1-(3,4-dichloro-5-methylphenyl)-2,2,2-trifluoroethan-1-one (C201) To 5-bromo-1,2-dichloro-3-methylbenzene (6.9 g, 29 mmol) in tetrahydrofuran (65 mL) cooled in an ice bath under nitrogen was added isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran (26.8 mL, 34.8 mmol). After 1 hour methyl 2,2,2-trifluoroacetate (3.79 mL, 37.7 mmol) was added. After 30 minutes, the ice bath was removed, and the solution was stirred for 1 hour. The reaction mixture was quenched with aqueous hydrochloric acid (2 N). The mixture was concentrated and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (SiO2, petroleum ether) provided the title compound as a white solid (5.9 g, 80%): 1H NMR (400 MHz, CDCl3) delta 8.00 (s, 1H), delta 7.83 (s, 1H), 2.51 (s, 3H); EIMS m/z 256 ([M]+).

According to the analysis of related databases, 431-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Barton, Thomas; Gao, Xin; Hunter, Jim; LePlae, JR., Paul R.; Lo, William C.; Boruwa, Joshodeep; Tangirala, Raghuram; Watson, Gerald B.; Herbert, John; (261 pag.)US2017/208803; (2017); A1;,
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Synthetic Route of 3196-15-4, The chemical industry reduces the impact on the environment during synthesis 3196-15-4, name is Methyl 2-bromobutyrate, I believe this compound will play a more active role in future production and life.

EXAMPLE 62a; Preparation of intermediate 2-(4-chloro-2-formyl-phenoxy)-butyric acid methyl ester; A mixture of 5-chloro-2-hydroxy-benzaldehyde (156 g, 1 mol), 2-bromo-butyric acid methyl ester (271 g, 1.5 mol), KI (2 g, 0.012 mol) and K2CO3 (276 g, 2 mol) in DMF (500 mL) was heated at 130 C. for 2 h. After cooled to room temperature, the mixture was concentrated. The residue was partitioned between EtOAc and water. The organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the title compound (240 g).

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

Reference:
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); A1;,
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Related Products of 15568-85-1, 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. 15568-85-1, name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, This compound has unique chemical properties. The synthetic route is as follows.

The 2- [4-(7-chloro-l,6-naphthyridin-4-yloxy)-2-methoxyphenyl] acetic acid used as a starting material was prepared as follows :-; 5-(Methoxymethylidene)-2,2-dimethyl-l,3-dioxane-4,6-dione (11.16 g) was added to a suspension of 2,6~dichloropyridine-4-amine (8.15 g) in isopropanol (125 ml) at ambient temperature. The resultant mixture was stirred and heated to 75C for 45 minutes. The mixture was cooled to 1O0C and diluted with diethyl ether. The precipitate was isolated. There was thus obtained 5-[(2,6-dichloropyridin-4-ylamino)methylidene]-2,2-dimethyl- l,3-dioxane-4,6-dione (15.5 g); 1H NMR Spectrum: (DMSOd6) 1.7 (s, 6H)5 7.9 (s, 2H), 8.75 (S5 IH), 11.25 (s, lH).

The chemical industry reduces the impact on the environment during synthesis 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
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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 443-26-5 as follows. Recommanded Product: Ethyl 2-fluorobenzoate

As described for the general reaction of ethyl 2-fluorobenzoate with amines set forth in Tetrahedron, 53, 7557-7576 (1997), ethyl 2-fluorobenzoate was reacted with pyrazole by refluxing N, N-dimethylformamide to give ethyl 2-(1-pyrazolyl)-benzoate, as a thick yellow oil. Anal. Calc’d: for C12H12N2O2: C, 66.7; H, 5.6; N 13.0: Found: C, 66.5: H, 5.4: N, 12.9; Mass spectrum (ES) 217.2 (M+H). A sample (7.02g) of this compound and 8.42 ml of 5N NaOH in 40 ml of ethanol-tetrahydrofuran (2:1) was refluxed for 2 hrs and the solvent removed.The residue was made acidic (pH6) with 2N citric acid and the precipated solid was filtered to obtain 3.7g of product. The pH of the filtrate was adjusted to 4.5 and extracted with ethyl acetate. The extract was concentrated to dryness to give 1.5g of product. The two crops were combined to give 5.2g of 2-(1-pyrazolyl)benzoic acid, mp 140-142C. To the preceding compound (2.07 g) in 5 ml CH2Cl2 (chilled in an ice bath )was added 11.1 ml of a 2 Molar solution of oxalyl chloride in CH2Cl2 and 0.085 ml of N,N-dimethylformamide. The mixture was allowed to warm to room temperature and stirred for 4 hours. The solvent was removed and 25 ml of toluene added (twice) and removed under vacuum to give 2-(1-pyrazolyl)benzoyl chloride as a yellow solid.

According to the analysis of related databases, 443-26-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth Holdings Corporation; EP1147095; (2004); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 94994-25-9, name is Methyl 4-formylbicyclo[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 94994-25-9, Recommanded Product: Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate

Step A:Diethyl (ethylsulfonomethane)phosphonate (1.12 g, 4.6 mmol) (Popoff, I. C. et al. J. Org.Chem. 34: 1128-30 (1969)) and 4-carbomethoxybicyclo[2.2.2] octane-1-carboxaldehyde (1-1) (0.82 g,4.2 mmol) (Adcock, W., Kok, G. B. J. Ore. Chem. 50: 1079-1087 (1985)) were dissolved in 8 mL ofabsolute methanol. The mixture was placed under nitrogen atmosphere, cooled in an ice-bath, andtreated with 0.5M solution of sodium methoxide in methanol (8.8 mL, 4.4 mmol). The reaction mixturewas kept under reflux for 4 h, then cooled to room temperature, concentrated under diminished pressure,then treated with 2 mL of water and allowed to sit in the refrigerator overnight. The mixture was filteredand the solid washed with a small amount of cold 1:1 MeOH/water. The resulting white solid wascollected and dried under vacuum to give the unsaturated sulfone 1-2. MS (ESI”1″) = 287 (M+l).

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-formylbicyclo[2.2.2]octane-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2006/17542; (2006); 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. 2475-80-1, name is Methyl 2-amino-5-methoxybenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-amino-5-methoxybenzoate

Step A: To a solution of (3a.R, 5R, 6aS) -5- (2- (trifluoromethyl) phenyl ) hexahydrocyclopenta [c] yrrole-2 { 1 ) -carbonyl chloride (0.100 g, 0.315 mmol) in THF (1.8 raL) was added i-Pr2NEt (0.041 g, 0.315 mmol ) and methyl 2-amino-5-methoxybenzoate (0.057 g, 0.315 mmol) . The resulting solution was heated at 68 C for 18 h. The reaction was diluted with 0 (30 mL) and extracted with EtOAc (4 x 30 mL) . The combined organic extracts were concentrated under reduced pressure. The resulting residue was chroraatographed over silica gel (0% to 100% EtOAc in hexanes) to give methyl 5-methoxy-2- ( (3ai?, 5R, 6aS) -5- (2- (trifluoromethyl ) henyl ) octahydrocyclopenta [ c] yrrole-2- carboxamido) benzoate as a white film (94.9 mg, 65%): 1H NMR (500 MHz, CDClj) delta 10.27 (s, 1H) , 8.59 (d, J= 9.5 Hz, 1H) , 7.60 (d, J= 8.0 Hz, 1H) , 7.55-7.46 (m, 3H) , 7.30-7.26 (m, 1H) , 7.13 (dd, J = 9.5, 3.5 Hz, 1H) , 3.92 (s, 3H> , 3.81 (s, 3H) , 3.76-3.72 (m, 2H) , 3.59-3.48 (m, 3H) , 2.93-2.85 (m, 2H) , 2.41-2.33 (m, 2H) , 1.68-1.60 (ra, 2H) ; MS (ESI+ ) m/z 463 E + 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; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; PETRUKHIN, Konstantin; CIOFFI, Christopher; JOHNSON, Graham; DOBRI, Nicoleta; FREEMAN, Emily; CHEN, Ping; CONLON, Michael; ZHU, Lei; WO2014/152018; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 619-45-4, name is Methyl 4-aminobenzoate, 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 619-45-4, Computed Properties of C8H9NO2

i) Methyl 4-aminobenzoate (25 g.) in dry chloroform (250 ml.) was treated dropwise with sulphuryl chloride (10 ml.) and the mixture heated at reflux for 4 hours. A further supply of sulphuryl chloride (10 ml.) was added and heating continued for a further 2 hours. The reaction mixture was poured onto ice and 2N sodium hydroxide solution was added. The organic solution was separated and the aqueous phase extracted with ethyl acetate. The combined organic solution was dried (anhydrous magnesium sulphate) and evaporated to give methyl 4-amino-3,5-dichlorobenzoate as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-aminobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; The Wellcome Foundation; The Regents of the University of California; US5502073; (1996); A;,
Ester – Wikipedia,
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