Author: Jessica.F

Application of 33353-68-3,Some common heterocyclic compound, 33353-68-3, name is 3,5-Dichloro-2-methoxyaniline, molecular formula is C7H7Cl2NO, 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.

6,8-Dichloro-5-methoxy-2H-benzorein ,2,41thiadiazin-3(4H)-one 1 ,1 -dioxide (lnt-24) A 250 mL round-bottomed flask was charged with chlorosulfonyl isocyanate (0.717 ml) in nitropropane (40 ml) to give a colorless solution at -40 C under nitrogen. After 10 min, a solution of 3,5-dichloro-2-methoxyaniline (1220 mg) in nitropropane (20 ml) was added to the reaction mixture. After 10 min, the reaction was warmed to 0 C. After 30 min, aluminum chloride (1 101 mg) was added to the reaction mixture. After 5 min, the reaction mixture was warmed to 100 C. After 45 min, the reaction mixture was poured in ice/water (400 mL) and stirred for 1 h. The solids were filtered and washed with water and hexanes, and dried in a vacuum oven overnight to obtain the titled compound (391 mg). LCMS m/z 297.1 (M+H).

The synthetic route of 33353-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); A1;,
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Electric Literature of 621-62-5, 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. 621-62-5, name is 2-Chloro-1,1-diethoxyethane belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 4-bromo-6-chloropyridazin-3-amine (15.7 g, 75.3 mmol), 2-chloro-1,1-diethoxyethane (13.9 g, 90.3 mmol) and PTSA (17.2 g, 90.3 mmol) in isopropanol (150 mL) was heated to 80 C. for 20 h. After cooling to room temperature, the solution was concentrated in vacuo. The resulting mixture was treated with a saturated NaHCO3 solution (300 mL), extracted with dichloromethane (200 mL×3), dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give 8-bromo-6-chloroimidazo[1,2-b]pyridazine (17.2 g, 98%) as an orange solid. LC-MS: [M+H]+, 231.9, 233.9, tR=1.46 min.

The synthetic route of 2-Chloro-1,1-diethoxyethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
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Related Products of 54730-35-7, These common heterocyclic compound, 54730-35-7, name is 3,5-Dichloro-4-methylaniline, 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.

Preparation 2; 5-bromo- 1 ,3-dichloro-2-methylbenzene; Suspend the 3,5-dichloro-4-methylaniline in 48percent HBr (5 mL) and water (5 mL) and heat with a heat gun until the mixture is near the boiling point. Cool the slurry to room temperature and then cool to 00C with an ice/brine bath. Add a solution of sodium nitrite (109 mg, 1.58 mmol) in water (2 mL) dropwise. After the addition is complete, stir the reaction an additional 15 min in the cold bath. Add a solution of CuBr (1.08 g, 7.53 mmol) in 48percent HBr (2 mL) and heat the rapidly stirring reaction to 500C for 1 hour. Cool the reaction to room temperature, dilute the reaction with ethyl acetate and discard the aqueous layer. Wash the organic layer with water and brine, dry with MgSO4, filter through celite and concentrate to an orange residue. Purify the residue by silica gel chromatography eluting with hexanes to afford 164 mg (45percent) of the product as a yellow solid.

The synthetic route of 54730-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/127763; (2007); A2;,
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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. 320-60-5, name is 2,4-Dichloro-1-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., SDS of cas: 320-60-5

Example 3; R-(+)-[2-(2,4-Dichloro-phenyl)-2-(4-fluoro-phenyl)-6-fluoro-benzo[1,3]dioxol-5-yl]-morpholin-4-yl-methanone; Preparation of 2,4-dichloro-4′-fluoro-diphenyldichloromethane; To a cooled (0 C.) suspension of aluminium trichloride (2.02 g, 15 mmol, 3.0 eq.) in 1,2-dichloroethane (7 mL) was slowly added 2,4-dichlorobenzotrifluoride (1.1 g, 5 mmol) followed by fluorobenzene (0.483 g, 5 mmol, 1.0 eq.). The reaction mixture was stirred at 0-5 C. for 5 h, then poured onto ice and extracted with dichloromethane. The combined organic layer was washed with brine, dried over sodium sulfate and filtered. The volatiles were removed in vacuo, affording the title compound (1.63 g, quant.) as yellow oil. MS: m/e=325.0 ([M+H]+).

The synthetic route of 320-60-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Frei, Beat; Plancher, Jean-Marc; Roever, Stephan; Zimmerli, Daniel; US2006/293318; (2006); 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. 21402-26-6, name is 4-Bromo-3-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H5BrClN

EXAMPLE 53 9-(Trifluoromethyl)-1,2,3,6-tetrahydro-7H-[1,4]thiazino[3,2-g]quinolin-7-one (Compound 156, Structure 54 of Scheme XI, where R4=H) 6-Bromo-7-chloro-2-isopropoxy-4-(trifluoromethyl)quinoline (Structure 51 of Scheme XI). This compound was prepared according to General Method 11 (EXAMPLE 22) from 4-bromo-3-chloroaniline (2.06 g, 10.0 mmol), ethyl 4,4,4-trifluoroacetoacetate (2.30 g, 12.5 mmol) in 50 mL toluene followed by heating in 33 mL conc. H2SO4 to afford 2.08 g (64%) of 6-bromo-7-chloro-4-(trifluoromethyl)-quinolin-2(1H)-one, an off-white solid.

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 21402-26-6.

Reference:
Patent; Ligand Pharmaceuticals, Inc.; US6462038; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2162-98-3, 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. 2162-98-3, name is 1,10-Dichlorodecane belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-aminopyridine (1.5 g, 15.9 mmol) and 1,10-dichlorodecane (1.61 g, 7.95 mmol) in amyl alcohol (26mL) was stirred and refluxed under N2 for 21 h. After cooling to room temperature, white precipitate formed was filtered off and washed with acetone/water to yield 2.4 h(75%) of APDE-8, which was further purified by crystallization from ethanol [Mp 278-282 C. 1H NMR (500 MHz,DMSO-d6) delta 1.17-1.26 (m, 12 H), 1.70-1.75 (m, 4 H),4.10 (t, 4 H, J = 6.0 Hz), 6.87 (d, 4 H, J = 6.5 Hz), 8.20 (d,4H, J = 6.0 Hz), 8.23 (s, 4 H, NH2). MS m/z 327.1565(M-2Cl)+].

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, 1,10-Dichlorodecane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sharma, Arun K.; Krzeminski, Jacek; Weissig, Volkmar; Hegarty, John P.; Stewart, David B.; Journal of Antibiotics; vol. 71; 8; (2018); p. 713 – 721;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 467435-07-0, name is 4-Bromo-2-chlorobenzotrifluoride, 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. Safety of 4-Bromo-2-chlorobenzotrifluoride

Preparation of Intermediate ethyl 3-(3-chloro-4-(trifluoromethyl)phenyl)acrylate (I-85a) DABCO (86.4 mg, 0.7 mmol), Pd(OAc)2 (86.5 mg, 0.38 mmol), 4-bromo-2-chloro-1-(trifluoromethyl)benzene (5.0 g, 19.2 mmol) and ethyl acrylate (2.86 g, 28.9 mmol) were added to a stirred solution of K2CO3 (2.6 g, 19.27 mmol) in DMF degassed previously for 20 minutes. The resulting mixture was stirred for 1 hour at 110 C. The reaction was monitored by TLC (5% ethyl acetate in hexane). Purification by column chromatography on silica gel (5% ethyl acetate in hexane) afforded 5.0 g of the product (94.3% yield). 1H NMR (CDCl3, 400 MHz): delta 7.75-7.7 (d, 1H), 7.68-7.62 (d, 1H), 7.6 (s, 1H), 7.54-7.46 (d, 1H), 6.54-6.48 (d, 1H), 4.3-4.2 (q, 2H), 1.4-1.32 (t, 3H).

The synthetic route of 4-Bromo-2-chlorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (2014); A1;,
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Related Products of 1000577-58-1, 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 1000577-58-1 as follows.

l -Bromo-2,3-dichloro-5-fluorobenzene (1,4618 g, 5.99 mmol) and mPEG3-OH (1.1097g, 6.76 mmol) was mixed with toluene (25 mL) and removed the solvent. The remaining material was dried under high vacuum for a few minutes. The mixture was dissolved in anhydrous THF (20 mL). 60% Sodium hydride (0.3549 g, 8.87 mmol) was added. The resulting mixture was heated at 75 C for 3 h. The mixture was cooled to room temperature. Saturated ammonium chloride aqueous solution was added to quench the reaction. The mixture was concentrated to remove the organic solvent. The remaining mixture was extracted with dichloromethane (3 x 20 mL). The combined organic solution was washed with brine, dried over anhydrous sodium sulfate, concentrated. The residue was purified with biotage flash column using 15-100% ethyl acetate/hexane to afford the product (2.057 g, yield: 88%). NMR (500 MHz, Chloroform-i/) delta 7.17 (d, J = 2.9 Hz, 1 H), 7.05 (d, J= 2.8 Hz, IH), 4.16 – 4.07 (m, 2H), 3.89-3.83 (m, 2H), 3.77-3.65 (m, 6H), 3.60-3.55 (m, 2H), 3.41 (s, 3H).

According to the analysis of related databases, 1000577-58-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEKTAR THERAPEUTICS (INDIA) PVT. LTD.; NEKTAR THERAPEUTICS; SHARMA, PANKAJ; KHATRI, VIJAY KUMAR; GU, XUYUAN; SONG, YUAN; SHEN, MICHAEL LIXIN; SAUTHIER, JENNIFER RIGGS; ANAND, NEEL K.; KOZLOWSKI, ANTONI; ODINECS, ALEKSANDRS; RILEY, TIMOTHY A.; REN, ZHONGXU; MU. YONGQI; SHEN, XIAOMING; YUAN. XUEJUN; AURRECOECHEA, NATALIA; O’MAHONY, DONOGH JOHN ROGER; WO2015/92819; (2015); A2;,
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Chlorides – an overview | ScienceDirect Topics

1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, 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. Product Details of 1298031-94-3

8-Bromo-6-chloro-2-methyl-imidazo[l,2-b]pyridazine (250 mg, 1.01 mmol) was combined with CS2CO3 (700 mg, 2.15 mmol) in CH3CN (5 mL). To the mixture was added MeOH (0.2 mL). The mixture was stirred at room temperature for 4 h. The volatiles were removed from the reaction mixture. The residue was partitioned between EtOAc and H20. The organic layer was collected, concentrated and chromatographed on silica gel, eluting with 20- 100% EtOAc in hexanes to yield 6-chloro-8-methoxy-2-methyl-imidazo[l,2-b]pyridazine (180 mg, 90%). MS m/z 198.2, 202.2 [M+H]+.

The synthetic route of 1298031-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1298031-94-3,Some common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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 mixture of 8-bromo-6-chloro-2-methyl-imidazo[1,2-b]pyridazine (100 mg, 0.41 mmol, 1.0 eq.), benzyl alcohol (89 mg, 0.085 mL, 0.81 mmol, 2.0 eq.) and Cs2CO3 (400 mg, 1.2 mmol, 3.0 eq.) in acetonitrile (1.0 mL) was stirred at 88 C overnight, then cooled, diluted with ethyl acetate and filtered through Celite. The filtrate was concentrated and purified over silica with ethyl acetate in CH2Cl2 (0 to 10% gradient) to give 8-benzyloxy-6-chloro-2-methyl-imidazo[1,2-b]pyridazine (81 mg, 73% ). 1H NMR (CDCl3) d: 7.62 (d, J= 0.6 Hz, 1H), 7.46 – 7.53 (m, 2H), 7.36 – 7.44 (m, 3H), 6.41 (s, 1H), 5.39 (s, 2H), 2.48 (d, J= 0.6 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; ZHANG, Nanjing; BABU, Suresh; BARRAZA, Scott J.; BHATTACHARYYA, Anuradha; CHEN, Guangming; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; SYDORENKO, Nadiya; TURPOFF, Anthony; WOLL, Matthew, G.; YAN, Wuming; (0 pag.)WO2020/5877; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics