Category: chlorides-buliding-blocks

Electric Literature of 202197-26-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Roschangar et al. ,Use of lithium N,O-dimethylhydroxylamide as an efficient in situ protecting agent for aromatic aldehydes. Tertrahedron 2002, 58, 1657-1666). Preparation analogous (Nishino et al.; Process for producing 4-aminoquinazoline compound by chlorination of quinazolin-4-one or its derivative and animation. 2003) as follows: To a mixture of 6-iodo-lH-quinazolin-4-one (10) (6.8Og; 25.0 mmol), toluene (5.0 mL) and POCl3 (27.5 mmol; 2.60 mL) carefully triethylamine (27.5 mmol; 3.81 mL) was added. The mixture was heated to 80 0C for 2 h, cooled to room temperature, a solution of 3-chloro~4-(3- fluorobenzyloxy)phenylamine (15) (27.50 mmol; 6.92 g) in 2~butanone (20.0 mL) added and the mixture stirred at 80 0C for another hour. The mixture was cooled to 00C, the yellow precipitate was filtered off and added to a NaOH solution (IN; 150 mL) by stirring. After 30 min the yellow solid was filtered off, washed with water and a small amount of acetone and dried in vacuo. Yield (8.38 g; 66%) analytical pure sample. 1H-NMR (DMSO-[D6]): delta (ppm) = 5.26 (s, 2H), 7.15-7.22 (m, IH), 7.27 (d, IH, J = 9.1 Hz), 7.29-7.35 (m, 2H), 7.43-7.51 (m, IH), 7.56 (d, IH, J = 8.8 Hz), 7.74 (dd, IH, J = 9.1 Hz, 4J = 2.5 Hz), 8.02 (d, IH5 4J = 2.5 Hz), 8.12 (dd; IH, J = 8.8 Hz, 4J = 1.7 Hz)5 8.62 (s, IH), 8.96 (d, 4J = 1.7 Hz), 9.90 (s, IH, exchangeable).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; 4SC AG; WO2009/63054; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 102-49-8,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.

General procedure: To a stirred solution of tosylate 1 (100 mg, 0.29 mmol) in Acetone or CHCl3 (3 mL) was slowly added amine 2 (0.58 mmol) and ketone 3 (0.87 mmol). Then p-TsOH (25 mg, 0.145 mmol)was addedto the reaction mixture. The resultant mixture was stirred at 60 C for 24 h until the reaction was completed as indicated by TLC. The reaction mixture was concentrated in vacuo, and then extracted with saturated aqueous NaHCO3 and CH2Cl2. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 4 or 5 as syrups.

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

Reference:
Article; Yuan, Wen; Xia, Jianhui; Zhang, Xiaoke; Liang, Peng; Zhang, Jichao; Jiao, Wei; Shao, Huawu; Tetrahedron; vol. 72; 27-28; (2016); p. 3994 – 4000;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2162-98-3,Some common heterocyclic compound, 2162-98-3, name is 1,10-Dichlorodecane, molecular formula is C10H20Cl2, 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 8 20.6 g (0.1 mol) of 4-octylaminopyridine, 10.5 g (0.05 mol) of 1,10-dichlorodecane and 30 ml of white spirit (boiling point 155 to 200 C.) were combined and heated to 130 C. The exothermic reaction causes the temperature to increase to 155 C., and at the same time white crystal precipitate out. The reaction mixture was stirred for a further 4 hours at 140 C., and after cooling to room temperature the very fine crystal sludge was filtered over a filterpaper and washed with petroleum ether, giving a beige, solid mass. The reaction product octenidine dihydrochloride in this example is very difficult to filter off with suction since it is produced in very fine form.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,10-Dichlorodecane, its application will become more common.

Reference:
Patent; AIR LIQUIDE SANTE (INTERNATIONAL); US2001/16660; (2001); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 61881-19-4, The chemical industry reduces the impact on the environment during synthesis 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, I believe this compound will play a more active role in future production and life.

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:

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, 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Sci-Tech University; Chen Zhengkai; Hu Sipei; Yang Zuguang; (10 pag.)CN110467579; (2019); 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. 202925-07-3, name is 2-Chloro-1-fluoro-4-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-1-fluoro-4-methoxybenzene

A mixture of 3-chloro-4-fluoroanisole (2.52 g, 15.7 mmol, 1.0 eq.), silver trifluoroacetate (8.53 g,38.6 mmol, 2.5 eq.), iodine (7.94 g, 31.3 mmol, 2.0 eq.) and chloroform (100 mL) is stirred at r.t. for 16 h. The reaction mixture is filtered through a silica plug on a fritted funnel and rinsed with chloroform. The filtrate is washed successively with an aqueous solution of Na2S2O3, water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel to afford the expected product.

The synthetic route of 202925-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; LABEGUERE, Frederic, Gilbert; HENG, Rama; ALVEY, Luke, Jonathan; AMANTINI, David; BREBION, Franck, Laurent; DE CEUNINCK, Frederic, Andre; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene; PEIXOTO, Christophe; POP-BOTEZ, Iuliana, Ecaterina; VARIN, Marie, Laurence, Claire; (147 pag.)WO2017/211667; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 210532-25-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 210532-25-5 name is 3,5-Difluorobenzene-1-sulfonyl chloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(R)-N2-Indan-1-yl-4H-benzo[d][1,3]oxazine-2,5-diamine (example 2) (150 mg, 0.54 mmol) was dissolved in 5 mL pyridine and 3,5-difluoro-benzenesulfonyl chloride (112 mg, 0.53 mmol) was added. The reaction mixture was stirred at room temperature overnight. 1N HCl was added until pH5. The mixture was extracted three times with ethyl acetate (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The crude product was purified by a silica gel column chromatography with heptane/ethyl acetate 1:1 to give a white solid (24 mg, 9%), MS: m/e=456.0 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Difluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Kolczewski, Sabine; Roche, Olivier; Steward, Lucinda; Wichmann, Juergen; Woltering, Thomas; US2010/63042; (2010); A1;,
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

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

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

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