Month: January 2021

Synthetic Route of 61881-19-4,Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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: Add sodium acetate, trifluoroethylimidyl chloride (II), hydrazone (III), and 1 mL of organic solvent to the 35 mL Schlenk tube according to the raw material ratio in Table 1.Mix and stir well. After the reaction is completed according to the reaction conditions in Table 2, 2-4 hours,Add elemental iodine, continue the reaction for 1-2 hours, filter, and stir the sample in silica gel.After purification by column chromatography, the corresponding 5-trifluoromethyl-substituted 1,2,4-triazole compound (I) is obtained. The reaction process is shown by the following formula:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, its application will become more common.

Reference:
Patent; Zhejiang Sci-Tech University; Chen Zhengkai; Hu Sipei; Yang Zuguang; (10 pag.)CN110467579; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 33050-38-3, name is 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, molecular formula is C5H2Cl2N4, 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: 33050-38-3

General procedure: Appropriate 6-chloro-[1 ,2,4]triazolo[4,3-b]pyridazine (1 eq) or 6-chloro- [1 ,2,4]triazolo[3,4-a]phtalazine (1 eq), potassium carbonate (3 to 4 eq) and the appropriate phenol, thiophenol (1 to 4 eq, 1 eq is preferentially used when R1 = CI) were dissolved in ?,?-dimethylformamide under nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature or at 100-1 10C, or 5-30 minutes at 100-170C on microwave irradiation. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2S04, filtered and evaporated to dryness. The residue was purified by chromatography on silica gel, precipitated, triturated in the appropriate solvent, or used without further purification to obtain the desired 6-aryl-[1 ,2,4]triazolo[4,3-b]pyridazine, or 6-aryl-[1 ,2,4]triazolo[3,4-a]phtalazine.This protocol was used to prepare the following compounds: Cpd.1 -1 , Cpd.1 -3, Cpd.1 -4, Cpd.1 -7, Cpd.1 -8, Cpd.1 -9, Cpd.1 -10, Cpd.1 -1 1 , Cpd.1 -12, Cpd.1 -13, Cpd.1 -14, Cpd.2-1 , Cpd.2-3, Cpd.2-4 and other compounds of the invention that contain a biphenyloxy, a pyridinylphenyloxy, a thiazolylphenyloxy, or a thiopenylphenyloxy group in the 6-substituted position of the [1 ,2,4]triazolo[4,3-b]pyridazines or 6-substituted position of the [1 ,2,4]triazolo[3,4-a]phthalazine (but further information about conditions and purification are reported in Tables of Example 2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33050-38-3, its application will become more common.

Reference:
Patent; GENFIT; BOUROTTE, Maryline; DELHOMEL, Jean-Francois; DUBERNET, Mathieu; GOUY, Marie-Helene; WO2013/45519; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1005-56-7, A common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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: Phenyl chlorothionoformate (345 mg, 2.0 mmol), amine 2 (4.0 mmol) and water (15 mL) were added successively to a 50 mL round-bottom flask. The reaction mixture was stirred at room temperature for 1 h (monitored by TLC). After the reaction was complete, the solid was filtered off, washed with 10% HCl (2 ¡Á 20 mL) and deionised water(2 ¡Á 20 mL), and dried under vacuum to give the pure thiocarbamates 3. All products are known compounds and were identified by comparison of their physical and spectral data with those reported inthe literature.28

The synthetic route of 1005-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Zhengyi; Chen, Yuan; Yin, Yue; Wang, Zhiming; Sun, Xiaoqiang; Journal of Chemical Research; vol. 40; 11; (2016); p. 670 – 673;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

873-38-1, name is 2-Bromo-4-chloroaniline, belongs to chlorides-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. Application In Synthesis of 2-Bromo-4-chloroaniline

4-chloro-2-bromo-aniline (206 mg, 0.01 mmol) was dissolved in dimethylsulfoxide (20 mL). Under a nitrogen atmosphere, bis(pinacolato)diboron (3.8 g, 15 mmol), potassium acetate (2.5 g, 25.7 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (218 mg, 0.3 mmol) were added thereto, and the temperature was raised to 80 C. to allow the reaction to proceed for 24 hours. Water (100 ml) was added to the reaction solution, which was extracted with ethyl acetate (80 ml¡Á2). The organic phases were combined, washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:100 to 1:30) to give the title compound 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2i) as a white solid (2.0 g, yield 79%). 1H NMR (400 MHz, CDC3) delta 7.54 (s, 1H), 7.19-7.08 (m, 1H), 6.55 (d, 1H), 4.86 (s. 2H), 1.34 (s, 12H). LCMS m/z=254.0 [M+1].

The synthetic route of 873-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; Wei, Yonggang; QIU, Guanpeng; ZHENG, Suxin; LEI, Bolin; YU, Yan; CHEN, Yashu; (29 pag.)US2017/29423; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 69695-61-0 as follows. Recommanded Product: 69695-61-0

(e) Preparation of 5-Methanesulfonyl-pyridine-2-carboxylic acid (2-chloro-4-trifluoromethoxy- phenyl)-amide 7:2-Chloro-4-trifluoromethoxy-phenylamine (2.0 g, 9.29 mmol) in toluene (50 mL) was added to trimethylaluminum (2.0 M 4.65 mL) then methyl 5-(methylsulfonyl)picolinate 6 (1.0 g, 4.65 mol) was added and the mixture was heated to 80-90C for 2 h. The reaction was cooled down and IN HC1 solution (10 mL) was added to be acidic. Dichloromethane (100 mL) was then added and the organic phase was further washed with water (100 mL) and dried over sodium sulfate. The solvent was removed and the residue was mixed with ether (50 mL) and stirred for 0.5 h. The solid was filtered and dried to give 5-methanesulfonyl-pyridine-2-carboxylic acid (2- chloro-4-trifluoromethoxy-phenyl)-amide 7 as a light yellow solid. Yield: 1.26 g, 65%.1H-NMR (300 Hz, CDCI3) delta (ppm): 10.6 (s, 1H), 9.21 (m, 1H), 8.68 (dd, 1H), 8.52 (dd, 1H), 7.40 (dd, 1H),7.22 (m, 2H), 3.20 (s, 3H).

According to the analysis of related databases, 69695-61-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSLO UNIVERSITY HOSPITAL HF; HOLSWORTH, Daniel; WAALER, Jo; MACHON, Ondrej; KRAUSS, Stefan; VORONKOV, Andrey Edward; GOLDING, Louise; WO2012/76898; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 69695-61-0, These common heterocyclic compound, 69695-61-0, name is 2-Chloro-4-(trifluoromethoxy)aniline, 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.

An aqueous solution of 2-chloro-4-(trifluoromethoxy)phenylamine (9.0 g) was cooled at 0C, and concentrated hydrochloric acid (75 mL) was dropped slowly to its solution. The reaction mixture was stirred for 30 minutes, and sodium nitrite (3.73 g) was added to the reaction mixture. The reaction mixture was stirred for 40 minutes. An aqueous mixture solution of copper cyanide (4.65 g) and sodium cyanide (7.08 g) which been cooled off in 0C was added to the reaction mixture, and the reaction mixture stirred at room temperature for an hour. The reaction mixture was poured into 5N aqueous solution of sodium hydroxide which been cooled with ice, and extracted twice with ethyl acetate. The organic layer was washed by a saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (high flash-SI, size 4L (made in Yamazen corporation), n-hexane?ethyl acetate/n-hexane=1/8) to obtain a title compound (7.36 g) having the following physical data. TLC:Rf 0.50 (n-hexane/ethyl acetate=20/1); 1H-NMR(CDCl3): delta 7.18 (m, I H), 7.37 (m, 1 H), 7.72 (d, J=8.6 Hz, 1 H).

The synthetic route of 69695-61-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO Pharmaceutical Co., Ltd.; EP2154139; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

10061-02-6, name is trans-1,3-Dichloropropene, belongs to chlorides-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: 10061-02-6

PREPARATION OF DIAZOKETONE (4C)Ester (2a) (4.3 g, 28 mmol) was added to a solution of sodium hydride (60% dispersion in mineral oil, 1.4 g, 36 mmol) in DMF (50 mL) at 0 C. The mixture was stirred for 10 min before the addition of 1,3-dichloro-1-propene (1:1 E,Z-mixture, 92%, 4.1 mL, 42 mmol) and warmed to r.t. After 4 h, the reaction was quenched by addition of sat. NH4Cl solution (20 mL), and the reaction mixture was extracted with Et2O (100 mL*2). The organic phase was washed with brine (50 mL), dried over MgSO4, filtered and concentrated. Purification of the residue by flash column chromatography (hexanes-EtOAc, 3:1) gave methyl ester (4a) (1.8 g, 30%).Rf 0.53 (hexanes-EtOAc, 1:1). 1H NMR (500 MHz, CDCl3): d 6.19 (dt, J=1.2, 13.2 Hz, 1H), 5.94 (dt, J=7.9, 13.3 Hz, 1H), 3.85 (s, 3H), 3.16 and 3.02 (ABq, J=18.2 Hz, 2H), 2.67 2.56 (m, 2H), 2.21 (s, 3H). 13C NMR (125 MHz, CDCl3): d 202.7, 168.6, 125.5, 123.7, 118.2, 54.1, 48.9, 44.6, 38.1, 29.6.

The synthetic route of 10061-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SNU R&DB FOUNDATION; US2011/28741; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

93765-83-4, name is 1-Bromo-5-chloro-2-fluoro-4-methylbenzene, belongs to chlorides-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. Safety of 1-Bromo-5-chloro-2-fluoro-4-methylbenzene

To a solution of 1-bromo-5-chloro-2-fluoro-4-methylbenzene (11.3 g, 50 mmol) in dry THF (100 mL) was added isopropylmagnesium chloride (30 mL, 2 M) dropwise. After stirring at room temperature for 30 min, dry CO2 was added and the mixture was stirred at room temperature for additional 30 min. The reaction was quenched by sat. NH4Cl and extracted with EtOAc (100 mL*3). The combined organic layers were washed with water (50 mL*3), dried over anhydrous Na2SO4, filtered and concentrated to give the desired product (4.7 g, 49%). LCMS (ESI) m/z: 187.0 [M-H]-.

The synthetic route of 93765-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENON PHARMACEUTICALS INC.; GENENTECH, INC; Chowdhury, Sultan; Dehnhardt, Christoph Martin; Focken, Thilo; Grimwood, Michael Edward; Hemeon, Ivan William; Jia, Qi; Ortwine, Daniel; Safina, Brian; Sun, Shaoyi; Sutherlin, Daniel P.; Zenova, Alla Yurevna; US2013/317000; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 623-12-1,Some common heterocyclic compound, 623-12-1, name is 1-Chloro-4-methoxybenzene, molecular formula is C7H7ClO, 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: An oven-dried Schlenk tube was charged with the aryl halide (2 mmol) and amine (2.5 mmol), FeOA-Pd (0.05 g, 0.04 mmol, 1.5 mol%), base (3 mmol), solvent (5 mL) and additive. The resulting mixture was stirred for the appropriate time and temperature. After reaction completion the reaction mixture was then cooled to room temperature and the catalyst separated using a magnet, taken up in Et2O (4 mL), and washed with brine (5 mL). The resulting solution was dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloro-4-methoxybenzene, its application will become more common.

Reference:
Article; Rafiee, Ezzat; Ataei, Ali; Joshaghani, Mohammad; Tetrahedron Letters; vol. 57; 2; (2016); p. 219 – 222;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 622-86-6, name is (2-Chloroethoxy)benzene, belongs to chlorides-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 622-86-6, Recommanded Product: 622-86-6

General procedure: A solution of 3-imidazolyl-4-chromanone-(E)-oxime (4, 0.75 mmol) in dry DMF (1.5 mL) was mixed with a suspension of NaH (18 mg, 0.75 mmol) in dry DMF (1.5 mL). The reaction mixture was stirred at room temperature for 0.5 h. Then, a solution of phenoxyethyl chloride derivative 6 (0.825 mmol) in dry DMF (1 mL) was added gradually and stirring was continued at room temperature for 2 days. After completion of the reaction, the reaction mixture was poured into water (20 mL) and left in refrigerator overnight. The separated viscous oil was dissolved in propan-2-ol (2 mL) and treated with 65% HNO3 (0.07 mL) and the mixture was left in a fridge to form nitrate salts. The precipitated crystals were separated and wash with cold propan-2-ol to give pure compound 7.

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, (2-Chloroethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Babazadeh-Qazijahani, Mojtaba; Badali, Hamid; Irannejad, Hamid; Afsarian, Mohammad Hosein; Emami, Saeed; European Journal of Medicinal Chemistry; vol. 76; (2014); p. 264 – 273;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics