Tag: M.W=100-200

These common heterocyclic compound, 2033-24-1, name is 2,2-Dimethyl-1,3-dioxane-4,6-dione, 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. 2033-24-1

The Meldrum’s acid [1] (50.0 g, 347 mmol) and trimethyl orthoformate [2] (184 g) were charged into a 500 mL four-necked flask and heated under reflux for 1 hour. After completion of the reaction, the solvent was removed by an evaporator, and the crude product was recrystallized in a hexane / tetrahydrofuran mixed solvent to give 43.7 g of the compound [66] (yield: 68%).

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 2033-24-1.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; MINAMI, SATOSHI; (157 pag.)TWI588139; (2017); B;,
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6962-92-1, These common heterocyclic compound, 6962-92-1, name is 4-Chlorobutyl acetate, 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.

Examples 2 to 13 The process of Example 1 was repeated in a similar manner except that 0.4 mmol of each of the boron compounds as shown in Table 1 was used in place of p-methoxyphenylboronic acid and 0.30 mmol of each organic halide as shown in Table 1 was used in place of 1-bromooctane and reaction was conducted for the noted period of time in Table 1.

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 6962-92-1.

Reference:
Patent; Sumitomo Chemical Co.,Ltd.; EP1439157; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

623-70-1, 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. 623-70-1, name is Ethyl (E)-but-2-enoate, A new synthetic method of this compound is introduced below.

To a round bottom flask containing ethyl (2E)-but-2-enoate (10.9 g, 87.6 mmol) and CCl 4 (100 mL) were added NBS (17 g, 96 mmol) and AIBN (4.3 g, 26 mmol). The reaction mixture was stirred at 80 for 12 h. The reaction mixture was diluted with DCM and extracted with saturated NaHCO 3, water, and brine. The organic layer was dried over anhydrous Na 2SO 4 and evaporated to dryness to yield the title compound (7.5 g, 44% yield) as an oil.

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Reference:
Patent; JANSSEN PHARMACEUTICA NV; CAI, Min; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin D.; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (999 pag.)WO2018/103058; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

63106-93-4, name is 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one, 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. 63106-93-4

Diethylamine (1 .56 g, 21 .3 mmol) is added dropwise to a suspension of aluminum trichloride (1 .38 g, 10.4 mmol) in toluene (9.6 mL), cooled to 0 C under magnetic stirring and in nitrogen atmosphere, checking that the internal temperature of the system does not exceed 15 C. The obtained solution is maintained at 25 C for about 30 minutes, then a toluene (2 mL) solution of lactone A (1 .50 g, 8.6 mmol) is slowly added. The mixture is maintained under magnetic stirring at 25 C up to complete conversion (about 2 hours), then poured into water (7.2 mL) previously cooled to 5 C, checking that the internal temperature does not exceed 25 C. The obtained phases are separated and the aqueous phase extracted with toluene. The organic phase is filtered on a panel of activated carbon and celite, and concentrated at reduced pressure until a residue of 2.50 g (containing about 2.10 g of the desired product) is obtained, which is used in the next step without any further purification.

Statistics shows that 63106-93-4 is playing an increasingly important role. we look forward to future research findings about 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one.

Reference:
Patent; QUIMICA SINTETICA, S.A.; BARRECA, Giuseppe; ROMANO’, Bruno Gaetano; (16 pag.)WO2016/71303; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 369-26-6, name is Methyl 3-amino-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 369-26-6

To a suspension of compound 21 (1.01 g, 6 mmol) in hydrochloric acid (13 ml, 37%) at 0 C was added a cold solution of sodium nitrite (0.50 g, 7.2 mmol) in water (5 ml) maintaining the temperature below 5 C. The resultant solution was stirred in an ice bath for 30 min before the addition of a solution of tin(II) chloride dihydrate (4.06 g, 18 mmol) in hydrochloric acid (5 ml, 37%) maintaining the temperature below 5 C. The resultant suspension was stirred at 0 C for 3 h and the suspension filtered and then dissolved in DCM, washed with saturated NaHCO3, dried over by MgSO4 to get the compound 22 (1.01 g, 92%). 1H NMR (CDCl3, 400 MHz): delta 7.79-7.77 (m, 1H), 7.46 (s, 1H), 7.04-6.99 (m, 1H), 5.48 (br, 1H), 3.91 (s, 3H) 3.62 (br, 2H). ESI-HRMS: m/z calcd for C8H9FN2O2 [M+H]+ 185.0682 found 185.0664.

The synthetic route of 369-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Chaocao; Htan, Bu; Fu, Shitao; Ma, Chunmiao; Gan, Quan; Tetrahedron; vol. 75; 30; (2019); p. 4010 – 4016;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

42726-73-8, Name is tert-Butyl methyl malonate, 42726-73-8, 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.

Potassium hydroxide (2.00 g, 36.0 mmol), tert-butyl methyl malonate (1.22 mL, 7.2 mmol) and DCM (20 mL) were added to a 100-mL flask under inert atmosphere. The mixture was stirred at room temperature until the solution became white then PhI(OAc)2 (1.93 g, 6.0 mmol) was added and stirred at room temperature for 2 hours. The solution was filtered through a cotton plug and washed with small portions of DCM. The solvent was removed under reduced pressure and the remaining oil was placed under high vacuum for 2 hours. The oil crystallized and the resulting solid was used without further purification. 1.038 g (46percent); off-white solid; m.p. 95-97¡ãC (dec.); 1H NMR (CDCl3; 600 MHz): delta 1.45 (s, 9H), 3.77 (s, 3H), 7.40-7.43 (m, 2H), 7.52-7.54 (m, 1H), 7.71-7.73 (m, 2H); 13C NMR (CDCl3; 150 MHz): delta 28.6, 52.5, 80.1, 114.5, 127.5, 130.3, 131.3, 131.5, 163.9, 164.4; HRMS: Calculated for C14H18IO4 (377.0250) [M+H]+, Found: 377.0255.

Statistics shows that tert-Butyl methyl malonate is playing an increasingly important role. we look forward to future research findings about 42726-73-8.

Reference:
Article; Stokes, Sean; Mustain, Rachel; Pickle, Lydia; Mead, Keith T.; Tetrahedron Letters; vol. 53; 30; (2012); p. 3890 – 3893;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

64113-91-3, These common heterocyclic compound, 64113-91-3, name is tert-Butyl 2-aminobenzoate, 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.

A 12 L round bottom flask, equipped with a thermocouple, nitrogen adapter and a 1 L addition funnel, was charged with a solution [OF T-BUTYL 2-AMINOBENZOATE] (537g, 2.78 moles; lot 36648-tjb-40) in ethanol (1620 [ML,] 3 ml/g). To this golden solution was added water (615.6 [ML)] resulting in a biphasic mixture. This mixture was cooled to between 15 and 20 C with a cold-water bath. A 1.0 M solution of [ICL IN CHZCIZ] [(ALDRICH LOT #14127JO,] 3.11 L, 3.11 moles, 1.12 equiv. ) was charged in portions to the addition funnel and was added to the rapidly stirred mixture maintaining the temperature between 15 and [25 C.] The addition time was 2.25 hours and the temperature range observed was 16.5 to 20. [4 C.] The resulting red brown mixture was stirred at room temperature for 1 hour at which time the GC assay showed the reaction was complete. The reaction was diluted with 920 mL of water and quenched with 456 mL of [38%] aq. sodium bisulfite (Webb [CHEM LOT #10464519)] resulting in a slight exotherm to 24. [0 C.] This mixture was stirred for 15 minutes before separating the phases. The methylene chloride layer was combined with water (3.7L) and stirred for 15 minutes before separating the phases. A [NAOH] solution was prepared by diluting 10% [NAOH] [(460ML)] in water (2.3L). To the methylene chloride layer was added this dilute [NAOH] solution (2.1L). The pH of the basic phase was 6.56. The phases were separated and the methylene chloride layer was concentrated to a low volume in vacuo at 16 torr using a bath temp of [45 C. PYRIDINE] (4L) was added, and the resulting solution was concentrated to ca. 1.0 mL/g [IN.] vacuo at 16 torr using a [62 C] water bath. The low volume pyridine/product mixture was diluted with pyridine to the target volume of 3. 1L (3. [5 ML/G).] A sample [(LOML)] was concentrated removing the pyridine on the rotovap and high vacuum to yield 3.12 g of an orange brown solid of 96% potecy by GC. GC assay of pyridine solution indicated that neither EtOH nor methylene chloride were present, so the solution was taken on directly into the next step.

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 64113-91-3.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, 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. 42122-44-1

To a stirred solution of the product of Step AD2 (9 g, 0.05M) in dry toluene (90 ml) under nitrogen, nitro ethane (8.5 ml, 0.050M) was added, followed by triethylamine (3.4 ml, 0.025M). Then a solution of phenyl isocyanate (6 g, 0.05M) in dry toluene was added to the RM at 80 C. After the addition was over the stirring was continued for overnight at 80 C. The RM was cooled under ice bath, filtered and the filtrate was concentrated under vacuum. The resulting mass was taken in ethyl acetate (75 ml) and washed with water (2¡Á20 ml), 5% NH4OH (40 ml), dried over anhydrous sodium sulphate and concentrated under vacuum to get crude product which was purified by column chromatography over silica gel (60-120) using PE/EtOAC (9.9/0.1) as eluent to afford isoxazole ester 3.7 g (32%).

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 42122-44-1.

Reference:
Patent; Gerritz, Samuel; Shi, Shuhao; Zhu, Shirong; US2006/287287; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

7270-63-5,Some common heterocyclic compound, 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C6H6N2O4, 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: To a solution of diazo compound 1 (0.5 mmol) and alkynes (1.1 mmol) in toluene (2 mL) was added rhodium(II) pivalate (0.01 mmol). The reaction mixture was stirred at 60C for 0.5-5 h. The solvent was evaporated in rotary evaporator under reduced pressure to give the residue. The residue was purified by flash column chromatography on silica gel to give the product. 4.2.17. 2,4-Di(phenanthren-9-yl)-6H-furo[2,3-b]pyran-6-one (5p). Reaction of 1 (85 mg, 0.5 mmol) and 9-ethynylphenanthrene (222 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 5p (98 mg, 40%) as a solid: mp 156-158 C; 1H NMR (300 MHz, CDCl3) delta 8.81-8.62 (4H, m), 8.23 (1H, d, J=7.5 Hz), 8.04-7.85 (5H, m), 7.78-7.53 (8H, m), 6.52 (1H, s), 6.42 (1H, s); 13C NMR (75 MHz, CDCl3) delta 159.3, 158.4, 154.2, 147.8, 131.8, 130.7, 130.6, 130.5, 130.5, 130.2, 129.1, 129.0, 128.8, 128.5, 128.4, 128.0, 127.9, 127.5, 127.4, 127.2, 127.1, 126.9, 126.9, 126.8, 126.7, 125.9, 125.3, 124.8, 123.1, 122.9, 122.5, 122.3, 107.5, 106.0, 101.3; IR (KBr) 2923, 1714, 1646, 1533, 1411, 1266, 1166, 1032, 962, 826, 750 cm-1; HRMS m/z (M+) calcd for C35H20O3: 488.1412. Found: 488.1411.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, its application will become more common.

Reference:
Article; Somai Magar, Krishna Bahadur; Lee, Yong Rok; Kim, Sung Hong; Tetrahedron; vol. 69; 44; (2013); p. 9294 – 9302;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

927-68-4, The chemical industry reduces the impact on the environment during synthesis 927-68-4, name is 2-Bromoethyl acetate, I believe this compound will play a more active role in future production and life.

Step D2-azidoethyl acetateN3^0AC [00269] A mixture of 2-bromoethyl acetate (500 muIota, 4.54 mmol) in N,N-dimethylformamide (DMF) (2.0 mL) was treated with sodium azide (295 mg, 4.54 mmol) and then heated to 70 C for 2 hours. The mixture was diluted with water and then extracted with ether. The extracts were washed with water, then brine, dried over sodium sulfate, filtered and concentrated to afford the title compound as a colorless liquid. 1H NMR (400 MHz, CHLOROFORM-d) d = 4.29 – 4.19 (m, 2 H), 3.53 – 3.44 (m, 2 H), 2.1 1 (s, 3 H).

The chemical industry reduces the impact on the environment during synthesis 2-Bromoethyl acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; DE LA ROSA, Martha Alicia; HAYDAR, Simon, N.; JOHNS, Brian Alvin; VELTHUISEN, Emile Johann; WO2012/102985; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics