Author: Jessica.F

Synthetic Route of 367-22-6, 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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

4.1.1 Ethyl 2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetate (6a) To a stirred solution of 3-fluoroaniline (1.11 g, 10.0 mmol) in CHCl3 (30.0 mL) was added dropwise N-chlorosuccinimide (NCS) in CHCl3 (20.0 mL) at 0 C. The mixture was stirred at 0 C for 42 h. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in Et2O. The mixture was washed with water, and dried over MgSO4. Concentration under reduced pressure followed by flash chromatography over silica gel with EtOAc/n-hexane gave 4-chloro-3-fluoroaniline (259.4 g, 18% yield) as crystalline solids. To a stirred solution of the above aniline (259.4 mg, 1.78 mmol) in THF (8.9 mL) were added at 0 C ethyl chloroglyoxylate (237.3 muL, 2.14 mmol) and Et3N (296.6 muL, 2.14 mmol). The mixture was stirred at room temperature for 12 h. After the precipitate was filtrated off, the filtrate solution was concentrated under reduced pressure. The residue was dissolved in EtOAc, and washed with 1.0 M HCl, saturated NaHCO3 and brine, then dried over MgSO4. Concentration under reduced pressure to provide the title compound 6a (435.2 mg, 99% yield) as brown crystals, which was used without further purification. 1H NMR (500 MHz, CDCl3) delta 1.44 (t, J = 7.50 Hz, 3H), 4.43 (q, J = 7.50 Hz, 2H), 7.24-7.25 (m, 1H), 7.35-7.40 (m, 1H), 7.70-7.75 (m, 1H), 8.93 (br, 1H); 13C NMR (125 MHz, CDCl3) delta 13.0, 64.1, 108.5 (d, J = 26.3 Hz), 115.9 (d, J = 3.75 Hz), 117.3 (d, J = 18.8 Hz), 130.9 (d, J = 10.0 Hz), 135.9, 153.9, 158.1 (d, J = 246.3 Hz), 160.5; HRMS (ESI), m/z calcd for C10H10ClFNO3 (MH-) 244.0182, found 244.0183.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Narumi, Tetsuo; Arai, Hiroshi; Yoshimura, Kazuhisa; Harada, Shigeyoshi; Hirota, Yuki; Ohashi, Nami; Hashimoto, Chie; Nomura, Wataru; Matsushita, Shuzo; Tamamura, Hirokazu; Bioorganic and Medicinal Chemistry; vol. 21; 9; (2013); p. 2518 – 2526;,
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Application of 1871-57-4,Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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.

To a suspension of sodium hydride (purity> 55%, 11.4 g) in N, N-dimethylformamide (150 mL),Under ice cooling, add 3-chloro-2-chloromethyl-1-propene (12.7 mL, CAS number: 1871-57-4),After stirring for 10 minutes at the same temperature,2- (tert-Butoxycarbonylamino) -1-ethanolA solution of (19.3 g, CAS number: 26690-80-2) in tetrahydrofuran (150 mL) was added dropwise over one and a half hours, and the mixture was stirred at room temperature for two and a half hours.The reaction solution was ice-cooled, water was added, and the mixture was extracted 3 times with diethyl ether,The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.After filtration and concentration under reduced pressure, the obtained residue is purified by silica gel column chromatography (n-hexane / ethyl acetate) to give the title compound.(16.0 g) was obtained as an oil.

The synthetic route of 1871-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Healthcare Co Ltd; Naito, Hiroyuki; Suzuki, Takayuki; Murata, Takeshi; Kawai, Junya; Higuchi, Saito; (99 pag.)JP2020/45306; (2020); A;,
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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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

(iii) Preparation of N-[3-chIoro-4-[(3-fluorobenzyIoxy)phenyl]-6-iodo- quinazolin amine (3) Into a one liter four-necked round bottomed flask, 500mL of acetic acid, 50.0 g of N’- (2-cyano-4-iodo-phenyl)-N, N-dimethyl formamidine of the formula-(8) obtained according to the process given in the above step (ii) 51.0 g 3-chloro-4-(3′- fluorobenzyloxy)aniline were charged . The reaction mass was maintained at 115- 120 C for about 2 Hrs., the cooled to 25-35 C and quenched into ice cold water. The pH of the reaction mass was adjusted to basic by slow addition of aqueous ammonia solution and the reaction mass was filtered and dried at 70-75 C.Dry weight: 93.0 gPurity: 83.64% by HPLCThe purity of the product is enhanced by adopting the following procedure.

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; JYOTHI PRASAD, Ramanadham; ADIBHATLA KALI SATYA, Bhujanga rao; VENKAIAH CHOWDARY, Nannapaneni; WO2011/39759; (2011); A1;,
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Application of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

j00535j Compound rac**A2 (50 mg, 0.3 mmol) and 2,4-dichloropyrrolo[2,1-JI[1,2,4jtriazine (52 mg, 0.3 mmol) were dissolved in 2-propanol (1 mL). After stirring at room temperature for 3 hours, N,N-diisopropylethylamine (80 .iL, 0.5 mmol) was added, and the reaction mixture was stirred for 16 hours, concentrated onto silica and purified by column chromatography [chloroform: 7M NH3 in methanol = 1:0 to 9:11 to afford compound rac-6-int (59 mg, 64% yield). LCMS (1): tR=2.498 mi, (ES) m/z (M+H) = 333.0.

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); 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. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows., name: 5-(Chloromethyl)benzo[d][1,3]dioxole

Preparation of 1, 3-benzodioxol-5-ylmethyl isopropyl sulfone 7.8 g of 5-(chloromethyl)-1, 3-benzodioxol was dissolved in 20 ml of anhydrous tetrahydrofuran and 20 ml of diethyl ether and then added to magnesium at 0C, and reacted for 10 minutes. The reactant was heated to 50C and reacted for 1 hour. The reaction mixture was cooled to 0C and then slowly added to a flask containing [1, 3-bis (diphenylphosphino) propane] nickel (II) dichloride as a catalyst. After the addition of 3. 9 ml isopropane sulfonyl chloride, the mixture was reacted for 30 minutes and the reactant was heated to 50C and reacted for 1 hour. Then, its pH was adjusted to 7 with dilute hydrochloric acid. The resulting mixture was extracted with diethyl ether and distilled water, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was fractionated by column chromatography using ethyl acetate: n-hexane (1: 3), to give 0.6 g of the title compound of the following formula ld (Rf : 0.35, Yield: 5%). [Chemical Formula 1d] The compound was dissolved in CDC13 and TMS and then characterized by IH NMR spectroscopy. The result is as follows ; ‘H NMR 8 : 1.60-1. 62 (d, 6H, J=6.7Hz), 2.79 (s, 2H), 3.75-3. 78 (m, 1H), 5.91 (s, 2H), 6.66 (m, 3H)

According to the analysis of related databases, 20850-43-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HAN, Sang Min; LEE, Myung Hee; CHOI, Won Chul; WO2005/70915; (2005); A1;,
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Synthetic Route of 328-84-7, These common heterocyclic compound, 328-84-7, name is 3,4-Dichlorobenzotrifluoride, 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 2,3-dichloro-6-trifluoromethylbenzoic acid (Compound No. 11) STR17 83.4 g of 3,4-dichlorobenzotrifluoride was dissolved in 800 ml of dried tetrahydrofuran, and 250 ml of hexane solution of n-butyl lithium(1.6 mol/1) was added to the solution dropwise over 15 minutes at -78 C. under nitrogen atmosphere. Following to stirring the solution for 2 hours at -78 C., 50 g of dry ice was then gradually added to the solution at the same temperature. After elevating the temperature of the solution up to room temperature, 250 ml of cold water was added to the solution to separate the resulting solution, and the aqueous layer obtained was adjusted to an acidic condition of a pH value of 1 with concentrated hydrochloric acid while cooling. Then, the aqueous layer was extracted with ether, and the extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure, and the oily residue obtained was crystalized with n-hexane, washed, filtered, and dried to obtain 89 g of the title compound(mp. 88-89 C.).

Statistics shows that 3,4-Dichlorobenzotrifluoride is playing an increasingly important role. we look forward to future research findings about 328-84-7.

Reference:
Patent; Nippon Soda Co., Ltd.; US6054605; (2000); A;,
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Reference of 102-49-8, 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. 102-49-8, name is 3,4-Dichlorobenzylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethanone (3) (0.200 g, 0.54 mmol), and phenylmethanamine (0.058 g, 0.06 mL, 0.54 mmol) were dissolved in acetonitrile (10.0 mL). Triethylamine (5 equiv, 0.38 mL) was added to the solution, and the reaction mixture stirred at 60 °C for 24 h. Solvent was removed from the reaction by rotary evaporation. The resulting yellow oil was purified using column chromatography from 2percent MeOH/CH2Cl2 to afford N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (0.0978 g, 51percent) as a brown solid, decomp. 125 °C.

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, 3,4-Dichlorobenzylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dyson, Lauren; Wright, Anthony D.; Young, Kelly A.; Sakoff, Jennette A.; McCluskey, Adam; Bioorganic and Medicinal Chemistry; vol. 22; 5; (2014); p. 1690 – 1699;,
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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. 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, A new synthetic method of this compound is introduced below., Safety of 3-Chloropropan-1-amine hydrochloride

General procedure: Toa suspension of lawsone (0.87 g, 5.0 mmol) in ethanol(10 mL) were added sequentially: i) the corresponding amine (5.5 mmol) – andtriethylamine (5.0 mmol, 0.7 mL) in the case of 3-(chloropropyl)aminehydrochloride – and ii) the respective aldehyde (6.0 mmol). The reactionmixture was stirred at RT, in the dark for 12h, after which time the orangeprecipitate was filtered, washed with ethanol, diethyl ether and dried undervacuum.Forthe syntheses of 6a, 6b, 6e, 6f, 6g and 6h, which are more soluble than the other products, the reactionswere carried out in the same amount of ethanol, but using 10.0 mmol of lawsone,10.0 mmol of heptylamine and 12.0 mmol of aldehydes.Compounds4a, 5a, 8a, 4b, 5b, 4c, 5c, 4d, 5d, 6d, 7d, 8d, 9e, 5g, 4h and 5h were synthesized as describedpreviously.3-5

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:
Article; da Silva, Gustavo B.; Neves, Amanda P.; Vargas, Maria D.; Marinho-Filho, Jose D.B.; Costa-Lotufo, Leticia V.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3537 – 3542;,
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Related Products of 1005-56-7,Some common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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.

In a 30 ml eggplant type flask,Methyl alpha-L-rhamnopyranoside178.2 mg (1.0 mmol),Dioctyldichlorotin41.6 mg (0.10 mmol),Tetrabutylammonium iodide36.9 mg (0.10 mmol),Tetrahydrofuran10 ml was added,Followed by stirring.thisTo the mixed solution, phenyl chlorothionoformate0.175 ml (1.3 mmol) was added,Then,1,2,2,6,6-pentamethylpiperidine0.271 ml (1.5 mmol) was added,The reaction was carried out at 20 C. for 6 hours.After completion of the reaction,To the reaction solution was added saturated ammonium chloride aqueous solution (20 ml)The extraction operation was carried out three times with 20 ml of ethyl acetate.The organic phase (ethyl acetate phase) was washed with 20 ml of water,After washing with 20 ml of an aqueous sodium chloride solution,It was dried over anhydrous magnesium sulfate,After filtration,The solvent (ethyl acetate) was distilled off under reduced pressure.The residuePurification by silica gel chromatography(Developing solvent n – hexane: ethyl acetate = 5: 1), 299.2 mg (yield 95%) of methyl 3 – O – phenoxythiocarbonyl -alpha- L – rhamnopyranoside was obtained. The hydroxyl groups other than the 3-position are monophenoxythiocarbonylatedThe selectivity of methyl 3-O-phenoxythiocarbonyl-alpha-L-rhamnopyranoside was 100% because alpha-L-rhamnopyranoside was not obtained.

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

Reference:
Patent; NAGASAKI UNIVERSITY; TOKUYAMA CORPORATION; ONOMURA, OSAMU; MURAMATSU, WATARU; IWASAKI, FUMIAKI; (32 pag.)JP5669643; (2015); B2;,
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Reference of 32768-54-0, These common heterocyclic compound, 32768-54-0, name is 2,3-Dichlorotoluene, 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: In a 1L reactor,add 61.5 g of 2,3-dichlorotoluene, 3.075 g of azobisisobutyronitrile (5%), 215.25 g of 2-dichloroethane, heat the mixture at 75 C and add 44 g of bromine drop wise,reflux reaction till red bromine fades , Intermittent drip and 136.2g27.5% hydrogen peroxide continues to react till red bromine no longer generates. Add a 49.2g30% aqueous solution of sodium carbonate to the reaction solution, reflux reaction for 8 h ,at the same time recover1,2-dichloroethane.

Statistics shows that 2,3-Dichlorotoluene is playing an increasingly important role. we look forward to future research findings about 32768-54-0.

Reference:
Patent; Lianyungang Industry Investment Group Co., Ltd.; Jiang Honglai; Jiang Xiao; Han Yong; Zang Han; Zhu Chengjie; Shen Weiwei; (5 pag.)CN107032968; (2017); A;,
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