Tag: M.W=100-200

Related Products of 6482-34-4, A common heterocyclic compound, 6482-34-4, name is Diisopropyl carbonate, molecular formula is C7H14O3, 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 5 Synthesis of methyl 2,2,3,3-tetrafluoropropyl carbonate (the compound of the formula [I] where R1 =H and R2 =1,1,2,2-tetrafluoroethyl) In a flask (500-ml volume) equipped with 10 distillation columns, 2,2,3,3-tetrafluoropropanol (100 g, 0.76 mol), dimethyl carbonate (205 g, 2.3 mol) and a 28% sodium methoxide/methanol solution (1.4 g) were charged. The flask was heated to 120 C. to allow the starting materials to react for 10 hours while removing the methanol from the distillation columns by evaporation. After allowing the mixture to cool to room temperature, an aqueous solution of ammonium chloride was added to the mixture and the mixture was shaken to remove the sodium methoxide. The organic layer was washed with water, dried and distilled to give methyl 2,2,3,3-tetrafluoropropyl carbonate as a colorless liquid (70 g, yield 49%). The chemical structure of the produced compound was determined based on the IR and NMR absorbance spectra shown in FIG. 9 and FIG. 10 respectively and the mass spectrometry spectrum (M/e=190). The absorbance peaks of IR and NMR are shown below. IR (neat): 2964 (C–H), 1764 (C=O), 1446, 1396, 1277, 1204, 1106, 994, 834, 787, 662, 580, 534 cm -1 NMR (CDCl3 soln., delta ppm): 3.86 (s, 3H, OCH3), 4.53 (t, 2H, J=12.5 Hz, OCH2 CF2 CF2 H), 5.90 (tt, 1H, J=53.1 Hz, H=4.3 Hz, OCH2 CF2 CF2 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; Mitsui Petrochemical Industries, Ltd.; Sony Corporation; US5659062; (1997); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 18595-18-1, 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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of imidazo[1 ,2-a]pyridine-3-carboxylic acid (1 ) (4.09 g, 25.3 mmol) in dichloromethane (100 mL) and DMF (0.25 mL) at 0 C was added oxalyl chloride (4.15 mL, 48.0 mmol) dropwise over 10 minutes. The reaction was slowly warmed to room temperature and stirred until complete conversion was detected by LCMS. The reaction was subsequently reduced to dryness and suspended in dichloromethane (100 mL) and was added a solution of methyl 3-amino-4-methylbenzoate (2) (4.6 g, 27.9 mmol) in dichloromethane (100 mL) and triethylamine (7.1 mL) . Contents were stirred at room temperature for 4 hours and diluted with dichloromethane (100 mL). The reaction was washed with water, saturated NaHC03, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude solid was triturated with diethyl ether to remove excess aniline and dried to afford methyl 3-(imidazo[1 ,2-a]pyridine-3-carboxamido)-4- methylbenzoate (3) as a white solid. MS m/z 310.1 (M+1 ) +. To a suspension of 3-(imidazo[1 ,2-a]pyridine-3-carboxamido)-4-methylbenzoate (3) (5.43 g, 17.6 mmol) in THF (225 ml) and MeOH (150 mL) was added LiOH 3 M (17.5 mL) and water (50 mL). The reaction was stirred at room temperature for 12 hours then reduced in volume on roto-vap to remove THF and MeOH. The mixture was diluted with water (75 mL) and neutralized with HCI (17.5 mL of a 3M solution). The resulting precipitate was filtered, washed with water and dried under vacuum to afford 3-(imidazo[1 ,2-a]pyridine-3-carboxamido)-4-methylbenzoic acid (4) as a white solid. 1 H NMR (400MHz, c 6-DMSO) delta 10.0 (s, 1 H), 9.45 (dt, J = 6.8, 1 .2 Hz, 1 H), 8.58 (s, 1 H), 7.98 (d, J = 2.0 Hz, 1 H), 7.79 (dt, J = 9.2, 1 .2 Hz, 1 H), 7.76 (dd, J = 8.0, 1 .6 Hz, 1 H), 7.52 (ddd, J = 9.2, 9.2, 1 .2 Hz, 1 H), 7.43 (d, J = 8.0 Hz, 1 H), 7.17 (td, J = 6.8, 1 .2 Hz, 1 H), 2.35 (s, 3H). MS m/z 296.1 (M+1 ) +.

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

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 4518-10-9, 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. 4518-10-9, name is Methyl 3-aminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of methyl 3-aminobenzoate (4.53 g, 30.0 mmol) and triethylamine (3.54 g, 4.88 mL, 35.0 mmol) in dichloromethane (100 mL), at 0 C. while stirring, was added bromoacetyl bromide (6.66 g, 2.9 mL, 33.0 mmol) dropwise. After the addition, the mixture was stirred at room temperature overnight and passed through a short silica pad. The crude product, 3-(2-bromoacetylamino)benzoic acid methyl ester (8.09 g, 99.1%), obtained after the removal of the solvent (>99% by LC/MS, MS (ES+) m/z: 272, 274) was used without further purification.

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

Reference:
Patent; Wilde, Richard G.; Takasugi, James J.; Hwang, Seongwoo; Welch, Ellen M.; Chen, Guangming; US2006/167065; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 33993-24-7, name is Cyclopropanecarboxylic anhydride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H10O3

Example 3 3,6,14-Tris(cyclopropylcarboxy)oxymorphone A suspension of oxymorphone (1.56 g; 5.19 mmol), cyclopropylcarboxylic acid anhydride (4.0 g; 25.95 mmol), and toluene (20 mL) was stirred at 80 C. for 160 min. Then DABCO was added in one portion (1.16 g; 10.38 mmol) and the resulting mixture was stirred at 80 C. over 15 h. After this time the conversion was incomplete and an additional amount of anhydride (1.60 g; 10.38 mmol) was added and mixture was stirred at 80 C. for 5 h. Then the reaction mixture was allowed to cool down, concentrated in vacuo, and the excess anhydride was removed under high vacuum. The mixture was diluted with dichloromethane (20 mL), washed with sat. NaHCO3 (5 mL) and the aqueous layer was extracted with dichloromethane (3*5 mL). Combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. Column chromatography (eluent EtOAc?EtOAc+10% MeOH) afforded 2.37 g (90%) of the title compound as a white solid. This reaction could also be performed using cyclopropylcarboxylic acid chloride (less expensive) and triethylamine in ethyl acetate as the solvent at 80 C. to obtain 92% of the titled compound. mp 158-160 C. (EtOH); Rf 0.40 (ethyl acetate:hexane/1:1); [alpha]22D=-122.96 (c=1.0, CHCl3); IR(CHCl3) v 3025, 2934, 2849, 1743, 1716, 1440, 1387, 1100, 1032 cm-1; 1H NMR (600 MHz, CDCl3) delta 6.86 (d, J=8.2 Hz, 1H), 6.67 (d, J=8.2 Hz, 1H), 5.42 (dd, J=6.0, 1.6 Hz, 1H), 5.08 (s, 1H), 4.22 (d, J=6.0 Hz, 1H), 3.21 (d, J=18.8 Hz, 1H), 3.05 (dd, J=18.3, 6.2 Hz, 1H), 2.55 (dd, J=18.8, 6.2 Hz, 1H), 2.47 (dd, J=11.8, 4.7 Hz, 1H), 2.38 (ddd, J=12.3, 12.3, 5.2 Hz, 1H), 2.31 (s, 3H), 2.22 (ddd, J=12.0, 12.0, 3.4 Hz, 1H), 2.04 (d, J=18.4 Hz, 1H), 1.87 (m, 1H), 1.77-1.69 (m, 1H), 1.65-1.58 (m, 2H), 1.21 (m, 1H), 1.18 (m, 1H), 1.14-1.09 (m, 3H), 1.05 (m, 1H), 1.04-1.00 (m, 2H), 0.99-0.94 (m, 2H), 0.90-0.82 (m, 2H); 13C NMR (150 MHz, CDCl3) delta 174.08, 173.21, 172.47, 147.37, 143.85, 133.30, 131.59, 130.69, 122.69, 118.87, 116.56, 86.88, 81.02, 57.45, 47.06, 45.07, 42.87, 30.28, 27.27, 22.96, 14.52, 12.97, 12.81, 9.367, 9.23, 9.16, 9.05, 8.55, 8.43; MS (+EI) m/z (%): 41 (48), 56 (55), 69 (100), 86 (100), 124 (20), 167 (16), 437 (16), 505 (12); HRMS calcd for C29H31NO7 505.2101. found 505.21049.

According to the analysis of related databases, 33993-24-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Brock University; US2012/283444; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, 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 924-99-2, name: Ethyl 3-(dimethylamino)acrylate

) [1-(5-Bromo-2-chloro- 3-pyridin-3-yI)methanoyl]dimethylaminoacrylic acid ethyl esterA stirred suspension of 2-chloro-5-bromo pyridine-3-carboxylic acid (5 g) in DCM (50 mL) at 2O0C was treated with oxalyl chloride (2.8 mL) and DMF (1 drop). After 1 h the clear solution was evaporated and re-evaporated from toluene (2x). The acid chloride was re- dissolved in toluene (80 mL) and treated with triethylamine (4.7 mL) and ethyl 3- dimethylaminopropenoate (3.94 g). After stirring for 1 h at 9O0C the mixture cooled and poured onto ice. Saturated aqueous sodium hydrogen carbonate (50 mL) was added and the organic layer washed with water and brine, dried (MgSO4) evaporated and the residue purified by chromatography (silica gel, 50-100% Et2O in petroleum ether [b.p. 40-600C]) to give the title compound as a colourless gum, (6.45 g); ESMS m/z 361.0, 363.0, 365.0 [M+H] +, 315.0, 317.0, 319.0 [M-OEt] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-(dimethylamino)acrylate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/50940; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, 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. Recommanded Product: 33993-24-7

Example 1; General Procedure for Demethylation/Acylation; Tertiary amine (0.1 mmol, 1.0 eq.) was dissolved in acetic anhydride (1 ml) and Pd(OAc)2 (0.01 mmol, 0.1 eq.) added. The reaction was heated at 80 C. for 15 hours, cooled to room temperature and passed through a plug of silica using CHCl3:MeOH:NH4OH 80:20:1 as eluent. The volatiles were removed in-vacuo, and the residue suspended in NaHCO3. The aqueous phase was extracted with CHCl3, and the combined organic extracts washed with 1M HCl and brine before being dried over magnesium sulphate, filtered and the volatiles removed in-vacuo to yield the acyl product.It will be understood by a person skilled in the art that the above description for Example 1 is provided for the general procedure. The examples shown below in Examples 1a-1j follow the general procedure outlined above, and shown in Scheme I from compound 3 to 7, but include the use of different sources of palladium and different amounts of Pd(OAc)2, where applicable, and the use of different solvents, as indicated in the table below.; Example 2; Reactivity of a Series of Anhydrides; The reactivity of a series of anhydrides was explored following the general procedure outlined in Example 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33993-24-7, its application will become more common.

Reference:
Patent; Brock University; US2009/5565; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 4630-80-2, The chemical industry reduces the impact on the environment during synthesis 4630-80-2, name is Methyl cyclopentanecarboxylate, I believe this compound will play a more active role in future production and life.

Example 2; 4-(4-(Benzyloxy)phenyl)-6-cyclopentyl-1H-pyrazolo[3s4-b]pyridin-3-amine Step 1:[00144] Sodium hydride (1.378 g, 59.9 mmol, 60% suspension in mineral oil) and ethanol (2.0 mL) were added to a solution of methyl cyclopentanecarboxylate (6.14 g, 47.9 mmol) and l-(4-metfaoxyphenyl)ethanone (6,00 g, 40.0 mmol) in THF (200 mL). The mixture was heated to reflux for 11 h, quenched with water (100 mL) and acidified to pH~2 with 1 N HCl. The THF solvent was evaporated in vacuo. The residue was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine (25 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with hexanes and small amount of toluene and eluting with 0-15% ethyl acetate in hexanes, gave i-cyclopentyl-3-(4-methoxyphenyl)propane~1,3-dione as yellow liquid (5.494 g, 56% yield). MS (ES+) m/z: 247 (M+H); LC retention time: 4.510 and 3.578 min, likely a mixture of keto and enol forms (analytical HPLC Method A).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUAN, Jingwu; JIANG, Bin; LU, Zhonghui; WO2011/19780; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 443-26-5, name is Ethyl 2-fluorobenzoate, 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. COA of Formula: C9H9FO2

REFERENCE EXAMPLE 191 Methyl 4-(4-Methoxybenzenesulfonyl)-1-[2-(1-pyrazolyl)phenylcarbonyl]-7-methyl-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate 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 C12H12 N2O2: 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).

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

Reference:
Patent; American Cyanamid Company; US6544984; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 42122-75-8, These common heterocyclic compound, 42122-75-8, name is Methyl 5-amino-2-chlorobenzoate, 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 2-Chloro-N-(1 -hydroxy-cyclohexylmethyl)-5-phenylamino-benzamide1.1 2-Chloro-5-Dhenylamino-benzoic acid methyl esterCs2C03 (2.79 g), palladium(ll) acetate (82 mg), 2,2′-bis(diphenylphosphino)-1 ,1 ‘- binaphthalene (228 mg), iodobenzene (0.69 mL) and methyl-5-amino-2-chlorobenzoate (1.13 g) were placed in a flask and flushed with argon. Dioxane (18 mL) was added and the reaction mixture was heated to 100C for 24h. After cooling to RT, it was diluted with Et20, filtered over a pad of celite and the filtrate was concentrated in vacuo. The crude material was purified by CC (Hept/EtOAc 1/0 to 8/2) to give 1.18 g of the titled compound as a light yellow solid.LC-MS (A): tR = 1 .05 min; [M+H]+: 262.55.

The synthetic route of 42122-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; WO2012/114268; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 57625-74-8,Some common heterocyclic compound, 57625-74-8, name is Methyl 2-methyl-2-phenylpropanoate, molecular formula is C11H14O2, 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.

Step C. To a suspension ofAlCl3 (500.0 mg, 3.75 mmol) inCH2Cl2 at-10 C was added dropwise oxalyl chloride (476.0 mg, 3.75 mmol) inCH2C12. The mixture was stirred at this temperature for 30 min. Then a solution of 2-methyl-2- phenyl-propionic acid methyl ester (178.0 mg, 1.0 mmol) inCH2C12 was added. The resulted mixture was stirred at-10 C for 1 hr and rt overnight. The mixture was filtered through a pad of celite, the solvent and excess oxalyl chloride was removed under reduced pressure. The residue was dissolved in chlorobenzene and refluxed for 4 hr. Solvent was removed and the residue was dried to give2- (4- chlorocarbonyl-phenyl) -2-methyl-propionic acid methyl ester.

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-methyl-2-phenylpropanoate, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99276; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics