Tag: M.W=100-200

140-39-6, Adding some certain compound to certain chemical reactions, such as: 140-39-6, name is p-Tolyl Acetate, 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 140-39-6.

General procedure: Powdered anhydrous AlCl3 (186 g, 1.4 mol) was added little by little to acetic acid phenyl ester b1 (95.3 g, 0.7 mol) in a round-bottomed flask in an ice-water bath. The resultant mixture was heated to 120 C for 6 h in an oil bath. Then the reaction mixture was added a lot of crushed ice for hydrolysis. The new formed organic layer in the reaction mixture was extracted by EtOAc, dried over anhydrous Na2SO4, and filtered off by suction filtration. The solvent was removed under reduced pressure to give the crude product, which was then purified by chromatography on silica using petroleum ether/ethyl acetate as the eluent. o-hydroxyacetophenone c1 (20.1 g, 21%) was obtained

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 140-39-6.

Reference:
Article; Tu, Qi-Dong; Li, Ding; Sun, Yao; Han, Xin-Ya; Yi, Fan; Sha, Yibamu; Ren, Yan-Liang; Ding, Ming-Wu; Feng, Ling-Ling; Wan, Jian; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 2826 – 2831;,
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207346-42-7, A common heterocyclic compound, 207346-42-7, name is Methyl 2-amino-4,5-difluorobenzoate, molecular formula is C8H7F2NO2, 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 30; 2-(5-chlorothiophen-2-yl)-2-(‘4-(6-fluoro-7-(methylaminoV2,4-dioxo-l,2-dihvdroquinazolin- 3(4H)-ylN)-3-methoxybenzamido)acetic acid (51); Scheme 7; [0151] To difluoroanthranalide Ic (5.69 g, 30 mmol), was added phosgene in toluene ((1.9 M, 160 mL, 300 mmol). The reaction mixture was stirred at rt overnight, concentrated in vacuo, evaporated from toluene (20 mL), and dried under vacuum to afford a light beige solid 8a. The material was found to give the desired urea when treated with ammonia but was not otherwise characterized.

The synthetic route of 207346-42-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2008/36843; (2008); A2;,
Ester – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 14062-24-9, name is Ethyl 4-chlorophenylacetate, 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 14062-24-9. 14062-24-9

General procedure: Sodium hydride (60% in oil, 6.0g, 0.15mol) was added portionwise over a period of 15min to an ice-cold mixture of arylacetate (0.03mol) and ethyl formate (22.2g, 0.30mol) in dry Et2O (150mL). Once addition was complete, cooling bath was removed and the reaction mixture was left at room temperature for 12h and then carefully poured into cold water (200mL). The biphasic mixture was acidified with small portions of conc. aq. HCl until steady pH 2-3 was achieved. Layers were separated, organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to dryness. Hydroxyacrylates 1a30 (yield 81%) and 1b30 (90%) were purified by distillation. Compounds 1c30 (70%) and 1d31 (75%) were washed by decantation with several small portions of cold petroleum ether. Characterization data are given in ESI.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Ethyl 4-chlorophenylacetate.

Reference:
Article; Shestakov, Aleksandr N.; Pankova, Alena S.; Golubev, Pavel; Khlebnikov, Alexander F.; Kuznetsov, Mikhail A.; Tetrahedron; vol. 73; 27-28; (2017); p. 3939 – 3948;,
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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. 25662-28-6 name is Methyl 1-cyclopentene-1-carboxylate, 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. 25662-28-6

To a stirred solution of methyl cyclopent-1-enecarboxylate (2.0 g, 15.89 mmol) in DCM (15.0 mL) was added (benzyl((trimethylsilyl)methyl)amino) methyl methanesulfonate (4.0 mL, 15.88 mmol) at rt and the mixture stirred at 0 C. for 15 min followed by the drop wise addition of trifluoroacetic acid (0.50 mL). The mixture was then stirred for 16 h at rt. After completion of reaction (by TLC), solvent was evaporated, water added (50.0 mL) followed by extraction with EtOAc (3¡Á100 mL) and the combined organic layer washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 7% EtOAc:hexane to obtain the product as a light yellow liquid (1.50 g, 75% yield). MS: 260.16 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1-cyclopentene-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BIOTA EUROPE LTD.; US2012/88750; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

33993-24-7, 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. 33993-24-7, name is Cyclopropanecarboxylic anhydride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Will contain water (0.32 ml) with trifluoroacetic acid (4.2 ml) cooled to -5 C the solution, and ethyl-N-[(mesitylsulfonyl)oxy]ethaneimidate (2.29 g, 8.02 mmol) blending and the stirring the mixture at room temperature for up to 1 hour. The reaction mixture with ice-water (20 ml) then mixes and with dichloromethane (20 ml) extraction. The sodium sulfate machine in on the drying and filtering, and the obtained solution for the 0 C dropwise to 5-bromo-4-methylpyridin-2-amine (1 g, 1.79 mmol) in dichloromethane (15 ml) in solution. The mixture stirred at room temperature for 1 hour and then with diethyl ether (20 ml) incorporation. The precipitated solid is filtered out of the diethyl ether is used for cleaning. The solid for drying under high vacuum. This produced 1.22 g (theoretical value of 57%) of the 1,2-diamino-5-bromo-4-methylpyridinium-2,4,6-trimethylbenzolsulfonate. The 1,2-diamino-5-bromo-4-methylpyridinium-2,4,6-trimethylbenzolsulfonate (580 mg, 1.44 mmol) and cyclopropylcarboxylic acid anhydride (1.33 g, 8.65 mmol) in pyridine (2.5 ml) in solution in 100 C stirring up to 8 hours. The reaction mixture is concentrated in the rotary evaporator and the residual substance is dissolved in DMSO/water/b in nitrile. By this solution the sealing ripoll filter filtering and by preparative HPLC (eluents: acetonitrile/water with 0.1% trifluoro acetic acid the gradient) to be purified. This generating 279 mg (theoretical value of 69%) the subject compound.

The synthetic route of 33993-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROEHN, ULRIKE; ELLERMANN, MANUEL; STRASSBURGER, JULIA; WENDT, ASTRID; ROEHRIG, SUSANNE; WEBSTER, ROBERTALAN; SCHMIDT, MARTINAVICTORIA; TERSTEEGEN, ADRIAN; BEYER, KRISTIN; SCHAEFER, MARTINA; BUCHMUELLER, ANJA; GERDES, CHRISTOPH; SPERZEL, MICHAEL; SANDMANN, STEFFEN; HEITMEIER, STEFAN; HILLISCH, ALEXANDER; ACKERSTAFF, JENS; TERJUNG, CARSTEN; (148 pag.)TW2016/5809; (2016); A;,
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A common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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. 35180-01-9.

Example 1 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid, 1-[(isopropoxycarbonyl)oxy]methyl ester (compound 1) 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid (prepared by the method disclosed in U.S. Pat. No. 5,138,069) was reacted with trityl chloride to obtain 2-butyl-4-chloro-1-[2′-(1-triphenylmethyl-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid. To a 100 ml of one-necked flask, 0.523 g of 2-butyl-4-chloro-1-[2′-(1-triphenylmethyl-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid, 0.124 g of potassium carbonate, and 5 ml of N,N-dimethylacetamide were added in turn. The solution was stirred at the room temperature for 20 minutes. Then 0.562 g of 1-chloromethyl isopropyl carbonate was added and the mixture was reacted at 45-50 C. for 16 h. After the reaction was completed, the mixture solution was filtered, and 30 ml of water was added into the filtrate. The resulting mixture was extracted with 30 ml of ethyl acetate twice. The organic phase was dried and concentrated to give 1.724 g of oil, which was directly used in the next reaction without purification. 10 ml of dioxane and 5 ml of 4 mol/L HCl were added, and the resulting mixture was reacted at the room temperature for 16 h. After the reaction was completed, the solution was adjusted to pH 6-7 using aqueous sodium bicarbonate solution. The solution became turbid, and was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, concentrated to give 0.436 g of 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid, 1-[(isopropoxycarbonyl)oxy]methyl ester. 1H-NMR: (CDCl3) deltaH (ppm): 0.89 (t, 3H, J=14.6), 1.24 (d, 6H, J=6.3), 1.37 (m, 2H, J=22.1), 1.69 (m, 2H, J=30.5), 2.64 (t, 2H, J=15.5), 4.81 (m, 1H, J=12.4), 5.54 (s, 2H), 5.86 (s, 2H), 6.95-7.64 (8H), 8.08 (d, 1H, J=7.42) ESI (+) m/z: 552.7

The synthetic route of Chloromethyl isopropyl carbonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guo, Jianhui; An, Dong; US2009/326024; (2009); A1;,
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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. 4897-84-1 name is Methyl 4-bromobutanoate, 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. 4897-84-1

(III) 4- (4-HYDROXYMETHYL-2-METHOXY-5-NITROPHENOXY) butyric acid allyl ester (52) 50 51 52 4- 4-FORMYL-2-METHOXYPHENOXY)-BUTYRIC ACID methyl ester (48); A solution of vanillin (47) (40.00 g, 262.89 mmol) and methyl-4- bromobutyrate (50.00 g, 276.18 mmol) in DMF (200 ML) was allowed to stir over potassium carbonate (51.53 g, 372.40 mmol) for 16 hours. Water was added to the reaction mixture at which time the product crystallised. The resulting mixture was filtered and dried in vacuo for 16 hours to afford the keto-ester (48) as a white solid (41.3g, 66%). MP = 57-59C. 1H NMR (250 MHz, CDCLG) 6 9.80 (s, 1H), 7.46-7. 40 (m, 2H), 6.97 (d, J = 8.1 Hz, 1H), 4.16 (t, J = 6.3 Hz, 2H), 3.92 (s, 3H), 3.70 (s, 3H), 2.57 (t, J = 7.2 Hz, 2H), 2.20 (pent, J = 6.7 Hz, 2H). 13C NMR (67.8 MHz, CDC13) 188.2 (C1), 173.7 (C12), 153.8 (Cquat. ), 152.0 (Cquat. ), 144.1 (Cquat. ), 125.8 (CMETHINE), 110.3 (C3), 108.5 (C6), 69.0 (C9), 57.0 (C8), 52.2 (C13), 30.6 (CLL), 24.5 (C10). It was decided to adopt the numbering system shown in the figure below for the molecule for ease of peak assignment IN 13C NMR. IR (cm-1) 3450,3332, 2952,1737, 1685,1587, 1467,1407, 1006, 938,864, 813,730, 656. MS (M+) 253. Anal. Calcd for C13 H16 Os : C, 61.90 ; H, 6.39. Found: C, 61.50 ; H, 6.39.

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

Reference:
Patent; SPIROGEN LIMITED; WO2005/23814; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

10601-80-6, Adding a certain compound to certain chemical reactions, such as: 10601-80-6, name is Ethyl 3,3-diethoxypropionate, 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 10601-80-6.

Example 22-(6-Chloro-pyridin-2-yl)-pyrimidin-4-ol (Intermediate compound); Ethyl-3,3-diethoxypropionate (1 g, 5.26 ml_) was dissolved in tetrahydrofuran (2 ml_) and aqueous hydrochloric acid (1.5 M) was added. The reaction mixture was stirred at room temperature for 4 hours and extracted with ethyl acetate.The combined organic layers were washed with brine, dried over sodium sulphate, filtrated and evaporated. Ethanol (20 ml_) was added and cooled to 0C.Crude theta-chloro-pyridine^-carboxamidine (560 mg, 1.44 mmol) in water (5 ml_) was added and the reaction mixture was stirred for 15 minutes at 0C. Sodium hydroxide (841 mg, 21.03 mmol) was added followed by additional stirring at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure. Water was added and extracted with chloroform. The combined organic phases were washed with brine, dried over sodium sulphate filtated and evaporated to give 2-(6-chloro-pyridin-2-yl)-pyrimidin-4-ol (350 mg, 53%) as a brownish solid.

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 3,3-diethoxypropionate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NeuroSearch A/S; WO2008/28935; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18595-14-7, A common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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 stirred solution of methyl 4-amino-5-methylbenzoate (85) (2.48 g, 15 mmol) in 25 mL of AcOH, NBS (3.0 g, 17 mmol)was added portionwise, the mixture was stirred for 1 h, diluted with water, extracted with DCM, washed with a saturated NaHCO3 solution, dried over a2S04, and rotovapped to yield 3.66 g of methyl 4-amino-3-bromo-5-methylbenzoate (86). XH NMR (CDC13, 400 MHz) delta 8.03 (s, 1H), 7.71 (s, 1H), 4.50 (brs, 2H), 3.87 (s, 3H), 2.25 (s, 3H).

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IVACHTCHENKO, Alexandre, Vasilievich; ALLA CHEM, LLC; IVASHCHENKO, Andrey, Alexandrovich; SAVCHUK, Nikolay, Filippovich; MITKIN, Oleg, Dmitrievich; (98 pag.)WO2017/39791; (2017); A1;,
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40800-65-5, 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. 40800-65-5 name is Ethyl 4-amino-3-methylbenzoate, 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.

1) 4-amino-3-methylbenzoic acid ethyl ester,The di-tert-butyl dicarbonate and absolute ethanol are stirred at 40 to 50 C for 4 to 6 hours to obtain a mixture I.

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; Shenzhen The Second People Hospital; Tan Hui; Li Weiping; Huang Guodong; (8 pag.)CN109761817; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics