Tag: M.W=100-200

Application of 54788-38-4, These common heterocyclic compound, 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, 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.

Referecne Example 1; (3-Bromophenyl) (4-chloro-2-hydroxy-5-methylphenyl) methanone; Aluminum chloride (20.4 g) was added to a solution of 3-chloro-4-methylanisole (20 g) in chlorobenzene (56 ml) at 20-30C, and then 3-bromobenzoyl chloride (28 g) was further added dropwise over about 30 minutes at 25 to 30C. After completion of addition, the mixture was stirred at 25C for 1 hour, and then heated at 40C for 1 hour. After the reaction was completed, the mixture was cooled, and toluene/tetrahydrofuran (1: 1,200 ml) was added dropwise at 20 to 30C. Then, 4N hydrochloric acid (80 ml) was added dropwise. The organic layer was separated, washed successively with 2N hydrochloric acid (60 ml) and a 10% aqueous sodium chloride solution. The organic layer was concentrated to 80 g. After methanol (100 ml) was added, the mixture was concentrated again to 90 g. Methanol (80 ml) was added to the residue, the mixture was stirred at room temperature for 30 minutes, and below 5C for 1 hour. Crysatls were collected, washed with cooled methanol (40 ml) and dried under reduced pressure to obtain the title compound (35.4 g, yield 85.1 %). H-NMR (300MHz, CDC13) 5 (ppm): 2.28 (3H, s), 7.12 (1H, s), 7.36-7. 42 (2H, m), 7.54-7. 57 (1H, m), 7.72-7. 80 (2H, m), 11.7 (1H, s).

The synthetic route of 54788-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/82879; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 7149-75-9,Some common heterocyclic compound, 7149-75-9, name is 4-Chloro-3-methylaniline, molecular formula is C7H8ClN, 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: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

The synthetic route of 7149-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, molecular formula is C6H5ClFN, 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.

Reference Example 152 1,1-dimethylethyl(4-chloro-3-fluorophenyl)carbamate A solution of 4-chloro-3-fluoroaniline (9.90 g, 68.0 mmol) and bis(1,1-dimethylethyl)dicarbonate (16.3 g, 74.8 mmol) in THF (100 mL) was stirred with heating at 60 C. for 15 hrs. Bis(1,1-dimethylethyl) bicarbonate (4.75 g, 21.8 mmol) was added again, and the mixture was further stirred at 60 C. for 3 days. The reaction mixture was concentrated under reduced pressure and crystallized from hexane to give the title compound as a white powder (11.8 g, 71%). 1H-NMR (300 MHz, DMSO-d6) delta: 1.48 (9H, s), 7.24 (1H, ddd, J=8.9, 2.4, 0.9 Hz), 7.45 (1H, t, J=8.8 Hz), 7.56 (1H, dd, J=12.2, 2.3 Hz), 9.73 (1H, s).

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 94-97-3, 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. 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: in EtOAc/MeOH (4:1) mixture solvent (2 mL), benzotriazoles 1 (0.3 mmol), sodium sulfinates 2 (0.54 mmol), NaBr (0.36 mmol) and mCPBA (0.39 mmol) were added successively. The suspension mixture was vigorously stirred at room temperature for 4 h. Upon completion, the reaction was quenched by addition of sat. aq. Na2S2O3 (2 mL), basified with sat. aq. Na2CO3(8 mL) and H2O (5 mL). The mixture was extracted with CH2Cl2 (3¡Á5 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified by TLC technique (3:1 (v/v) petroleum ether/ethyl acetate) to furnish sulfonylbenzotriazoles 3.

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, 5-Chloro-1H-benzo[d][1,2,3]triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Sixue; Zhang, Yikun; Yan, Jie; Synthetic Communications; vol. 46; 17; (2016); p. 1432 – 1437;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 108-41-8, 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. 108-41-8, name is 1-Chloro-3-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

m-chlorotoluene (5.1 g, 40 mmol),sodium bromate (4.6 g, 30.6 mmol),sodium bromide (6.3 g, 61.2 mmol), 1,2-dichloroethane (25 mL) was added to a reaction flask equipped with a stirred, reflux condenser, thermometer and tail gas absorber, heated to reflux and rapidly added 1/3 of the total volume of the initiator solution (0.15 g AIBN, dissolved (5 g) was slowly added dropwise with sulfuric acid (4.6 g, 46 mmol concentrated sulfuric acid diluted with 2 mL of water) and the remaining initiator solution was followed by gas chromatography. After completion of the reaction, the reaction was cooled to At room temperature, saturated sodium bisulfite solution (10mL) was added and stirred to red to fade. The mixture was allowed to stand, and the aqueous phase was extracted twice with 1,2-dichloroethane (10 mL x 2). The organic phases were combined and washed with saturated chlorine Sodium chloride solution washing, dry.The crude product was purified by column chromatography (elution solvent as petroleum ether) to give 10.2 g of m-chlorobenzyl dibromide in 90% yield.The product was a colorless liquid

The synthetic route of 1-Chloro-3-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Normal University; Xiao Xiaohui; Chen Yufeng; (12 pag.)CN107098791; (2017); A;,
Chloride – Wikipedia,
Chlorides – 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. 108-70-3, name is 1,3,5-Trichlorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1,3,5-Trichlorobenzene

General procedure: An oven-dried and argon-flushed pressure tube was charged with 1,3,5-trichlorobenzene, 1,2,4-trichlorobenzene or 1,2,3-trichlorobenzene (0.25 mmol), Pd2(dba)2 (1.25 mol%), cataCXium A (5.0 mol%), boronic acid (1.5 mmol) and K3PO4 (1.5 mmol) followed by anhydrous toluene (4.0 mL). The tube was sealed with a Teflon valve and the reaction mixture was stirred at 110 C for 24 h. The cooled reaction mixture was diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography.

The synthetic route of 108-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reimann, Sebastian; Ehlers, Peter; Sharif, Muhammad; Spannenberg, Anke; Langer, Peter; Tetrahedron; vol. 72; 8; (2016); p. 1083 – 1094;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, molecular formula is C6H4ClNaO2S, 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. category: chlorides-buliding-blocks

General procedure: Quinoline N-oxides 1 (0.3 mmol), sodium arylsulfinates 2 (0.45 mmol) and Fe(NO3)3 (0.09 mmol) in DMSO (3.0 mL) were added to a microwave reaction tube (5.0 mL). The reaction mixture was heated at 120 C for 20 min under microwave irradiation. After reaction completion, the solvent was distilled under vacuum. Ethyl acetate (10 mL) was added to the residue, and washed with saturated sodium chloride solution (3 ¡Á 30 mL). The organic phase was dried over anhydrous NaSO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired products 3 using ethyl acetate/petroleum ether (1:10 to 1:5) as the eluent. All compounds were confirmedby IR, 1H NMR, 13C NMR and MS.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14752-66-0, its application will become more common.

Reference:
Article; Mai, Wenpeng; Lv, Mingxiu; Zhang, Xiaofeng; Lu, Kui; Journal of Chemical Research; vol. 41; 12; (2017); p. 705 – 708;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 7006-52-2, These common heterocyclic compound, 7006-52-2, name is N-Methyl-3-chloroaniline, 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: S7 (0.35 g, 2 mmol) was dissolved in Et2O (5 mL) and converted into its hydrochloride salt by drop-wise addition of aq. HCl (1 M) in Et2O. The resulting precipitate was collected byfiltration, dried for 10 min, and used in the subsequent reaction. A mixture of S7 hydrochloride (212 mg, 1 mmol), S1 (185 mg, 1.1 mmol), and toluene (2 mL) was heated to 130 oC,stirred for 21 h, cooled to rt, and diluted with MeOH (5 mL). This solution was concentrated onto silicagel and purified on a silica gel column with gradient elution (EtOAc EtOAc-MeOH;4: 1 v/v). The fractions containing the desired guanidine were collected, concentrated under reduced pressure, andapplied to a second silica gel column eluted with Et3N-EtOAc-hexanes(5: 20: 75 by vol.) to afford 20 asa white solid

The synthetic route of 7006-52-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naumiec, Gregory R.; Cai, Lisheng; Pike, Victor W.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 2; (2015); p. 225 – 228;,
Chloride – Wikipedia,
Chlorides – 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. 6306-61-2, name is N-(2-Chloroethyl)propan-2-amine hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of N-(2-Chloroethyl)propan-2-amine hydrochloride

KOH (932 mg; 14.1 mmol) was dissolved in THF (7ml) and H20 (distilled, 0.17 ml). Intermediate 7 (341 mg; 0.95 mmol), then tetrabutylammonium bromide (76.5 mg, 0.24 mmol) were added to the mixture and stirred at room temperature for 5 minutes. The reaction mixture was heated at 50C for 1 hour. Then A/-(2-chloroethyl)-2-propanamine, hydrochloride (225 mg, 1.4 mmol) was added and the reaction mixture was stirred at 50C for 18 hours. A/-(2-chloroethyl)-2-propanamine, hydrochloride (76mg, 0.48 mmol) was added and the reaction mixture was stirred at 50C for 5 hours. Water was added and the reaction mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtered and evaporated to dryness. The crude product was purified by chromatography over silica gel (5muetaeta, mobile phase :Gradient from 0.2% NH4OH, 98% DCM, 2% MeOH to 0.8% NH4OH, 92% DCM, 8% MeOH). The desired product fraction was collected and the solvent was evaporated. The residue was dissolved in MeOH, 2 drops of HCI (37%) were added and the reaction mixture was stirred at room temperature for 2 minutes. The mixture was evaporated, taken up with CH3CN and crystallized from CH3CN to afford 41 mg of compound 1 (9%) as a chlorohydrate

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; ASTEX THERAPEUTICS LIMITED; BERDINI, Valerio; ANGIBAUD, Patrick Rene; WOODHEAD, Steven John; SAXTY, Gordon; WO2013/61074; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4535-90-4, name is 2-Chloro-N-methylethanamine hydrochloride, molecular formula is C3H9Cl2N, 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: 2-Chloro-N-methylethanamine hydrochloride

A mixture of tra/75-8-chloro-l-[4-(5-methyl-isoxazol-3-yl)-cyclohexyl]-5,6-dihydro-4H- 2,3,5, 10b-tetraaza-benzo[e]azulene (50.0 mg, 0.130 mmol), cesium carbonate (170 mg, 0.521 mmol) and 2-methylaminoethyl chloride hydrochloride (67.7 mg, 0.521 mmol) in acetonitrile (1.3 ml) was heated at 70 C for 20 h. After cooling to room temperature the reaction mixture was partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml). The layers were separated. The aqueous layer was extracted with three 5-ml portions of ethyl acetate. The combined organic layers were concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid) / methanol as eluent gave the hydro formate salt of the title compound, which was liberated by filtration over aminopropyl modified silica gel (10 g) with methanol (20 ml) as eluent. The filtrate was concentrated to dryness. The residue was redissolved in ethyl acetate, filtrated over cotton wool and concentrated to dryness to give the title compound (38 mg, 66%) as off-white solid. MS m/e: 441 ([M+H]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4535-90-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DOLENTE, Cosimo; SCHNIDER, Patrick; WO2011/141396; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics