Month: June 2021

Reference of 452-83-5,Some common heterocyclic compound, 452-83-5, name is 2-Chloro-5-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.

Step 1: 5-Fluoro-8 chloroquinoline To a mixture of (5.0 g) 2-chloro-5-fluoroaniline (commercially available, 6.0 g), glycerol (6.0 g) and m-nitrobenzene sulfonic acid sodium salt (11.0 g), was added 20 mL of 70% sulfuric acid dropwise. The reaction temperature was raised to 140 C. for 2 h. The mixture was then cooled, poured on ice water and filtered through Celite. The filtrate was neutralized with NaOH and extracted with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4 and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using 100% CH2Cl2 to give 3.7 g of the desired product of a yellow solid; MP=74-76 C.; MS (ES) m/z (relative intensity): 182 (M+H)+ (100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5-fluoroaniline, its application will become more common.

Reference:
Patent; Wyeth; US2007/299083; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1940-27-8, name is 4-Bromo-2,5-dichloroaniline, 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. Formula: C6H4BrCl2N

General procedure: A mixture of corresponding chloro derivative (IV) (4.2 mmol), the appropriate amine (4.2 mmol) and triethylamine (8.4 mmol) in dry acetonitrile was refluxed for 4 hours. The mixture was cooled, poured on crushed ice and filtered. The residue was washed with cold water and dried. The crude product was recrystallized from ethanol to get the titled compounds.

The synthetic route of 1940-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pradeep Kumar; Joshi, Shrinivas D.; Dixit, Sheshagiri R.; Kulkarni; Indian Journal of Heterocyclic Chemistry; vol. 25; 1; (2015); p. 75 – 82;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 6775-78-6, 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. 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows.

[0192] Step 2. Imidazo[1,2-blpyridazine-6-carboxylic acid methyl ester. A mixture of 6- chloro-imidazo [1 ,2-b]pyridazine (200 mg, 1.30 mmol, 1.00 equiv), bis(triphenylphosphine)palladium(II) dichloride (200 mg, 0.28 mmol, 0.22 equiv), and triethylamine (0.5 mL) in methanol (4 mL) was stirred under carbon monoxide (10 atm) in a 50-mL pressure reactor overnight at 110 C. The solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1/1) to give 100 mg (43%) of the titlecompound as a yellow solid. ?H NMR (300 MHz, CDC13) oe 8.16 (s, 1H), 8.08 (d, J = 9.6 Hz, 1H), 7.94 (s, 1H), 7.77 (d, J = 9.6 Hz, 1H), 4.09 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 6-Chloroimidazo[1,2-b]pyridazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; GOSSELIN, Francis; ZAK, Mark; ZHENG, Xiaozhang; WO2013/130935; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 60811-18-9, name is 4-Bromo-1-chloro-2-fluorobenzene, molecular formula is C6H3BrClF, 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. Product Details of 60811-18-9

[Example 23] (Preparation of 4′-(trans-4-n-pentyl-4-silacyclohexyl)-4-chloro-3-fluorobiphenyl) 6.5 g (20 mmol) of p-(trans-4-n-pentyl-4-silacyclohexyl) bromobenzene was dripped into a mixture of 0.5 g of magnesium (21 mmol) and 30 ml of THF to obtain a Grignard’s reagent. This solution was then dripped into a 50 ml THF solution of 4.2 g (20 mmol) of 4-chloro-3-fluoro-1-bromobenzene and a catalytic amount of tetrakis (triphenylphosphine) palladium (0) to obtain 4′-(trans-4-n-pentyl-4-silacyclohexyl)-4-chloro-3-fluorobiphenyl. This was then purified by means of chromatography to obtain 6.8 g of the target product (yield 98%). IR (liquid film) numax: 2953, 2916, 2870, 2108, 1479, 1396, 1200, 985, 879 and 812 cm-1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 60811-18-9, its application will become more common.

Reference:
Patent; Shin-Etsu Chemical Co., Ltd.; US5659059; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13726-14-2,Some common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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 substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below. 2-Chloro-/Y4-(4-chloro-3-methoxyphenyl)-6-methylpyrimidin-4-amine (SG2-053-01): This was prepared from 2,4-dichloro-6-methylpyrimidine (0.326 g), 4-chloro-3-methoxyaniline (0.331 mg), and DIPEA (0.420 mL) using procedure B (reaction time, 3 d). Ethyl acetate (15 mL) was added to the mixture which was then washed with water (15 mL). The aqueous layer was re-extracted with EtOAc (15 mL). The organic layers were combined, washed with water and brine (15 mL each), dried (Na2S04), and concentrated under reduced pressure. The resulting residue was purified via column chromatography (S1O2) eluting with hexanes/EtOAc (2:8 to 3:4 v/v) to give the title compound as an off-white solid (0.334 g, 59%). Mp: 168-169 C. NMR (400 MHz, DMSO-ifc): delta 10.02 (s, 1H, disappeared on D20 shake), 7.44 (d, / = 1.7 Hz, 1H), 7.36 (d, / = 8.6 Hz, 1H), 7.17 (dd, / = 8.6, 1.7 Hz, 1H), 6.59 (s, 1H), 3.83 (s, 3H), 2.28 (s, 3H). HPLC-MS (ESI+): m/z 286.1 [70%, (M35C137C1+H)+], 284.1 [100%, (M35C135C1+H)+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-methoxyaniline, its application will become more common.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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. Formula: C6H3BrClN3

General procedure: The corresponding 3-Bromo-6-chloro-imidazopyridazine (1.0 eq) was suspended in dioxane (0.5 mUmmol) and the appropriate n- boc diamine (2.7 eq) or amino alcohol (3 eq) was added. The mixture was heated under mw irradiation at 160C for 2h. Water was added and the mixture was extracted with AcOEt. The organic phase was separated, dried (Na2S04), filtered and evaporated till dryness. The residue was purified by Biotage flash column chromatography (eluent: 4 to 6% MeOH in DCM) to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13526-66-4, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; ALVAREZ ESCOBAR, Rosa Maria; VARELA BUSTO, Carmen; GARCIA GARCIA, Ana Belen; DIMITRIEVICH ZARICH, Natasha; BLANCO APARICIO, Carmen; RODRIGUEZ LOPEZ, Ana; OYARZABAL SANTAMARINA, Julen; BISCHOFF, James Robert; WO2013/1310; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 627-42-9,Some common heterocyclic compound, 627-42-9, name is 2-Methoxyethyl chloride, molecular formula is C3H7ClO, 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.

Sodium iodide (0.191 g, 1.273 mmol) was added to a stirred suspension of 5-fluoro-2- nitrophenol (4 g, 25.5 mmol), potassium carbonate (10.56 g, 76 mmol) and l-chloro-2- methoxyethane (5.1O mL, 56.0 mmol) in DMF (102 mL) at room temperature. The reaction mixture was allowed to stir at 800C overnight. Further l-chloro-2-methoxyethane (6.38 mL, 70.0 mmol) was added and the reaction mixture was allowed to stir at 800C for 4 h. Water and ethyl acetate were added and the organic layer was separated. The aqueous layer was neutralised with 1 N hydrochloric acid and extracted with ethyl acetate. The combined organic layers were washed with water, dried (MgSO4), filtered and evaporated to give a yellow oil. Column chromatography (petroleum ether/ethyl acetate 6:1) gave 4-fluoro-2-(2-methoxyethoxy)-l -nitrobenzene as a clear oil (2.26g, 39%).

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

Reference:
Patent; BIAL-PORTELA & COMPANHIA, S.A.; WO2009/84970; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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

Intermediate 15 N-(3,4-dichlorobenzyl)-7-methylimidazo[1,2-b]pyridazin-6-amine; To a mixture of 6-chloro-7-methylimidazo[1 ,2-b]pyridazine (0.20 g, 1.19 mmol) and 3,4-dichlorobenzylamine (0.24 ml_, 1.78 mmol) in 1 ,4-dioxane (7 ml_), were added sodium tert-butoxide (0.18 g, 1.91 mmol), (R)-(+)-2,2′- bis(diphenylphosphino)-1 ,1′-binaphthyl (0.06 g, 0.10 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.04 g, 0.06 mmol) at room temperature. The reaction mixture was heated at 1000C for 1 hour under microwave irradiation. The crude mixture was diluted with ethyl acetate/water and acidified with hydrochloric acid (2N) to pH 3, then extracted with ethyl acetate. The combined organic layers were dried (magnesium sulphate) and concentrated in vacuo. The crude mixture was purified by flash column chromatography (hexane/ethyl acetate 1 :4) followed by precipitation with diethyl ether to give N- (3,4-dichlorobenzyl)-7-methylimidazo[1 ,2-b]pyridazin-6-amine (0.25 g, 48percent yield) 1H NMR (300 MHz, CDCI3): delta 7.51 (1 H, s), 7.41 (2H, bs), 7.36 (1 H, s), 7.32 (1 H, d, J = 8.2 Hz), 7.15 (1H, dd, J = 2.3, 8.2 Hz), 4.47 (2H, d, J = 5.2 Hz), 4.43 (bs, 1 H), 2.14 (S, 3H). LCMS: 307 [M+1]. (MW: 307.2)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 102-49-8, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); WO2009/60197; (2009); A1;,
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. 821-10-3, name is 1,4-Dichlorobut-2-yne, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H4Cl2

General procedure: To a solution of diyne (50 mg) in dry solvent (5mL) in microwave reaction vessel propargyl halide 7b/c/e/f (2 equiv.) and Mo(CO)6 (5 mol%) were added andthe reaction mixture was irradiated in a CEM Discover microwave synthesizer for10 min. under standard conditions. Afterthe completion of reaction (TLC monitoring), the solvent was concentrated atreduced pressure and the crude product was purified by silica gel columnchromatography

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; Kotha, Sambasivarao; Sreevani, Gaddamedi; Tetrahedron Letters; vol. 56; 43; (2015); p. 5903 – 5908;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 4090-55-5,Some common heterocyclic compound, 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, molecular formula is C5H10ClO3P, 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 one-liter four-necked flask equipped with a stirrer, a thermometer, a thermostat, a dropping device (funnel), a hydrochloric-acid-recovering device (condenser connected with a water scrubber) and a reflux condenser, 226.8 g (0.9 moles) of dibutyl(1-hydroxy-1-methylethyl)phosphonate as an alcohol compound, 111.1 g (1.1 moles) of triethylamine as a hydrogen halide scavenger, 1.14 g (0.012 moles) of magnesium chloride as a catalyst and 20.8 g of toluene as an organic solvent were put in and stirred. The resulting mixed solution was retained at a temperature of 60C by using the thermostat, and the whole amount of each solution synthesized in Examples and Comparative Examples was added thereto gradually over 2 hours by using the dropping device. After completion of the addition, the resulting reaction mixture was stirred at a temperature of 60C for 1 hour to complete the reaction. Subsequently, 200 g of water was added to the resulting reaction mixture. The resulting solution was stirred at a temperature of 60C for 30 minutes, and then was allowed to stand to be separated into phases. Then, an aqueous phase was recovered to remove triethylamine hydrochloride generated as a by-product. Subsequently, 3.0 g (0.02 moles) of a 30% aqueous sodium hydroxide was added to the reaction mixture. The resulting solution was retained at a temperature of 20 to 60C by using the thermostat, and 97.1 g of a 35% hydrogen peroxide aqueous solution (1.0 mole as hydrogen peroxide) was added thereto gradually over 2 hours by using the dropping device. After completion of the addition, the resulting reaction mixture was stirred at a temperature of 60C for 1 hour to complete the reaction. Then, the resulting reaction mixture was washed with an aqueous hydrochloric acid solution and a sodium carbonate aqueous solution sequentially, and finally rinsed with water. The resulting reaction mixture was heated to a temperature of 100 to 140C, and the pressure was reduced to 100 torr (13.3 kPa) to recover water and toluene. Further, steam distillation was performed at a temperature of 100 to 140C under a reduced pressure of 20 torr (2.7 kPa) to remove low-boiling point components to obtain a transparent and colorless liquid (compound 1). The liquid obtained was analyzed by gas chromatography, and the result thereof was compared with gas chromatographic analysis results of cyclic phosphoric acid esters having known cyclic structures to confirm that the main component of the liquid obtained was each of the following cyclic phosphoric acid esters.

The synthetic route of 4090-55-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daihachi Chemical Industry Co., Ltd.; EP2495247; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics