Month: September 2021

Related Products of 84228-44-4, A common heterocyclic compound, 84228-44-4, name is Methyl 4-amino-3-chlorobenzoate, molecular formula is C8H8ClNO2, 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.

4-Amino-3-chloro-benzoic acid methyl ester (21.6 mmol) was saponified in EtOH (25 ml) and NaOH (IM5 25 ml) at reflux for 2h. The organic solvent was evaporated and pH adjusted to 4. The product was removed by filtration, washed with water and dried in vacuo to give A- amino-3-chloro-benzoic acid.Yield: 92%IH NMR (D6-DMSO): 6.15 (s, 2H); 6.79 (d, IH); 7.59 (dd, IH); 7.71 (d, IH); 12.37 (br s,IH).

The synthetic route of 84228-44-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2006/114093; (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. 346603-63-2, name is Methyl 2-methyl-3-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 346603-63-2

To a mixture of methyl 2-methyl-3-(trifluoromethyl)benzoate (15 g, 73.34 mmol) in acetic acid (100 mL) were added HNO3 (46 g) and bromine (12.8 g, 80.10 mmol). Then AgN03 (16.1 g, 2.5M in water) was added to above mixture over ~30 min. After stirred for 16 h at rt, The mixture was diluted with water. General Work-up Procedure 1 was followed. The residue was purified by Chromatography A to afford the title compound (14.0 g, 70%) as a colorless oil.

The synthetic route of 346603-63-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
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14062-18-1, name is Ethyl 2-(4-methoxyphenyl)acetate, 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. Recommanded Product: Ethyl 2-(4-methoxyphenyl)acetate

1 g of 4-methanesulfony benzoicacid, 970 mg of 4-methoxyphenylacetic acid ethyl ester, and 950 mg of carbonyldiimidazole were dissoved in 15 ml of dimethylformamide and 230 mg of sodium hydride were added dropwise to the solution and the mixture was reacted in room temperature for 12 hours. Afterwards, water was added to diute the resultant, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate to give 1.5 g of the title compound as a light yellow liquid(yield 83%).

The synthetic route of 14062-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cho, Il Hwan; Noh, Ji Young; Park, Sang Wook; Ryu, Hyung Chul; Lim, Jee Woong; Kim, Jong Hoon; Chae, Myeong Yun; Kim, Dal Hyun; Jung, Sung Hak; Park, Hyun Jung; Kim, Young Hoon; Min, In Ki; US2004/2532; (2004); A1;,
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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. 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6BrClO2

Preparation Example 10-1 To a solution of methyl 4-bromo-2-chlorobenzoate (1.25 g) in N,N-dimethylformamide (10 ml) was added sodium thiomethoxide (459 mg) under ice-cooling and the mixture was stirred for 2 hr. To the reaction mixture was added 1N hydrochloric acid and the resulting product was extracted 3 times with diethyl ether. The organic layers were combined, washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was applied to silica gel column chromatography (hexane/ethyl acetate=10/1) to give methyl 2-chloro-4-(methylthio)benzoate (835 mg) as a colorless oil. 1H-NMR(CDCl3): 2.49(3H, s), 3.90(3H, s), 7.11(1H, d, J=8Hz), 7.23(1H, s), 7.78(1H, d, J=8Hz).

According to the analysis of related databases, 185312-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; EP1142879; (2001); A1;,
Ester – Wikipedia,
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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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C7H13NO2

a) Ethyl 2-[(2,5-difluorophenyl)carbonyl]-3-(dimethylamino)-2-propenoateA solution of 2,5-difluorobenzoyl chloride (5.26 g, 29.8 mmol) in toluene (100 mL) was treated with ethyl-3-(dimethylamino)-2-propenoate (5.27 g, 36.8 mmol), followed by triethylamine (5.9 mL, 42.5 mmol). The mixture was stirred at 9O0C for 6.5 h then allowed to cool, and the precipitate removed by filtration. The filtrate was concentrated under reduced pressure to give a residue which was purified by flash chromatography (silica gel,50-100% diethyl ether in petroleum ether [b.p. 40-600C]) to give the title compound as a yellow oil (0.95 g); ESMS m/z 284.4 [M+H]+.

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2006/50942; (2006); A1;,
Ester – Wikipedia,
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Some common heterocyclic compound, 14062-30-7, name is Ethyl 2-(3-bromophenyl)acetate, molecular formula is C10H11BrO2, 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: C10H11BrO2

(3-Cyano-phenyl)-acetic acid ethyl ester A mixture of (3-bromo-phenyl)-acetic acid ethyl ester (9.15 g, 37.6 mmol), copper cyanide (5.06 g, 56.5 mmol), and 1-methyl-2-pyrrolidinone (80 mL) was placed into an oil bath heated at 120 C. behind a protective shield. The reaction was heated to 200 C. for 1 h and additional copper cyanide (spatula tip) was added. After heating for an additional 0.5 h, the reaction was cooled to room temperature. The reaction was diluted with EtOAc and the organic solution was washed with water/ammonium hydroxide solution (2:1 v/v) until the aqueous solution was no longer blue. The organic solution was washed with brine, dried (MgSO4), filtered, and concentrated. Flash chromatography (9:1 hexanes:EtOAc) provided (3-cyano-phenyl)-acetic acid ethyl ester (6.31 g) as a clear oil which solidified on standing. 1H NMR (400 MHz, CDCl3) delta7.57-7.50 (m, 3H), 7.42 (m, 1H), 4.15 (q, 2H), 3.63 (s, 2H), 1.24 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14062-30-7, its application will become more common.

Reference:
Patent; Pfizer Inc.; US6344485; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 14064-10-9, The chemical industry reduces the impact on the environment during synthesis 14064-10-9, name is Diethyl 2-chloromalonate, I believe this compound will play a more active role in future production and life.

MDPD was synthesized according to a procedure described by Shipp et al. Briefly, NaH (1.24 g, 0.0520 mol) was suspended in THF (10 mL) and cooled to 0° C. using an ice bath. A solution of diphenylamine (3.38 g, 0.0200 mol) in DMSO (18 mL) and THF (9 mL) was added and stirred for 1 h at 0° C. Carbon disulfide (2.84 mL, 0.0472 mol) was added and the solution stirred for a further 30 min at 0° C. The solution was then cooled using an ethylene glycol/CO2 bath prior to the addition of diethyl chloromalonate (3.23 mL, 0.0200 mol) and further stirring for 2 h at room temperature. Any remaining NaH was hydrolyzed with methanol and the product was extracted with diethyl ether. Volatiles were then removed and the product was purified using a silica column (ethyl acetate:hexane mix 10:90 to remove diphenylamine impurity, followed by 30:70 to elute product). The product was dried under vacuum to yield a yellow solid (yield 72percent).

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

Reference:
Patent; ARROWHEAD MADISON INC.; Wakefield, Darren H.; Rossi, Nicholas A.; Sheik, Dan; US2013/121954; (2013); A1;,
Ester – Wikipedia,
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6091-64-1, name is Ethyl 2-bromobenzoate, 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 C9H9BrO2

General procedure: The following experimental procedure for the partial alkynylation of ethyl benzoate to 1,3-diphenylprop-2-yn-1-one is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with phenyl acetylene (0.45 mL, 4.1 mmol) and THF (10 mL). After cooling to 0 C, n-BuLi (1.6 mL, 2.5 M in hexane, 4.0 mmol) was added dropwise and stirred for 1 h at room temperature. To the reaction mixture was slowly added morpholine (0.08 mL, 1.0 mmol) and stirred for 30 min at 0 C. Then, ethyl benzoate (0.14 mL, 1.0 mmol) was added and the mixture was stirred for 6 h again. The reaction was stopped by aqueous NH4Cl (aq) (10 mL) and extracted with diethyl ether (2 * 10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel yielded 1,3-diphenylprop-2-yn-1-one (175 mg, 85%). All products in Table 2 were confirmed by comparison with NMR data reported of authentic sample.7

The synthetic route of 6091-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Note; Shin, Won Kyu; Kim, Yu Ri; Im, So Hee; Jaladi, Ashok Kumar; Gundeti, Shankaraiah; An, Duk Keun; Bulletin of the Korean Chemical Society; vol. 39; 5; (2018); p. 683 – 686;,
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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. 6942-37-6, name is Methyl 5-amino-2-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

Step B. Preparation of methyl 2-bromo-5-(dimethylamino)benzoateTo a stirred solution of 5-amino-2-bromo-benzoic acid methyl ester (3.30 g, 14.35 mmol) in CH3OH (45 mL) containing CH2O (3.6 mL, 45.0 mmol) at room temperature was added a solution of NaBH3CN (945 mg, 14.35 mmol) and ZnCI2 (990 mg, 7.2 mmol) in CH3OH (45 mL). The reaction mixture was stirred at room temperature overnight, then concentrated. The residue was taken up in 0.1 N NaOH solution, extracted with EtOAc several times. The combined extracts were washed with H2O, brine, dried over dried Na2SO4, then filtered and concentrated. The residue was separated by silica gel column (hexane/EtOAc = 3 : 1) to give 2.991 g (92%) of methyl 2-bromo-5-(dimethylamino)benzoate as a yellow oil based on the partial recovery of (412 mg). methyl 2-bromo-5-(dimethylamino)benzoate, MS: m/z 259 (M + H)

The synthetic route of 6942-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2009/120826; (2009); 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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, A new synthetic method of this compound is introduced below., COA of Formula: C5H10O4

EXAMPLE 6 2,2-Dimethoxy-N-(3,4-dimethoxybenzyl)-acetamide 16.7 g. (0.1 mole) 3,4-dimethoxybenzylamine are contacted with 13.4 g. (0.1 mole) methyl 2,2-dimethoxyacetate for 3 hours. The reaction mass solidifies. The crude product is recrystallized from about 1 liter of a light petroleum ether fraction to give 19.4 g. of 2,2-dimethoxy-N-(3,4-dimethoxybenzyl)-acetamide in the form of white needles. A sample intended for analysis is sublimed at 70 C./0.03 mm.Hg. The yield is 72% of theory. The product has a melting point of 60 C. Infrared spectroscopy (CCl4) (cm-1): 3440 (NH), 2950 (CH3), 2850 (OCH3), 1680 + 1510 (CONH), 1600, 1460, 1115 + 1070 (CO) NMR (CDCl3): 6.84 (4H, singlet, Ha); 4.72 (1H, singlet, Hb); 4.38 (2H, doublet, Hc, J=6Hz); 3.87 (6H, singlet, Hd); 3.39 (6H, singlet, He) STR11 Mass spectrum: m/e 269 (M+), 237 (–CH3 OH), 222, 206 (M* at 209), 181, 166 (amine), 151 (tropylium), 75, 47, 31 (M* at 29.5) Analysis: C13 H19 NO5 (M.W. 269.3): calculated: C 57.98%; H 7.11%; N 5.20%; found: 57.95%; 7.15%; 5.17%

The synthetic route of 89-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; U C B, Societe Anonyme; US4041077; (1977); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics