Chlorides-buliding-blocks

Some common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, molecular formula is C6H4ClN3, 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. 6775-78-6

b) 3-Bromo-6-chloroimidazo[1 ,2-b]pyridazine; Bromine (3.8 mL, 74.19 mmol) was added dropwise to a solution of 6-chloroimidazo [1 ,2-b]pyridazine (Preparation 1 a, 4.8 g, 31.06 mmol) in glacial acetic acid (80 mL) and the resulting mixture was stirred at ambient temperature for 20 minutes. The precipitate formed was collected by filtration, washed with diethyl ether several times and dried in vacuo. The solid obtained was partitioned between ethyl acetate and a saturated aqueous solution of potassium carbonate. The organic layer was separated and washed with a saturated aqueous solution of potassium carbonate, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude was then treated with pentane, filtered and the solid obtained was dried in vacuo to yield the title compound (6.6 g, 92%) as a pale yellow solid.LRMS (m/z): 232 (M+1)+.1H-NMR delta (300 MHz, CDCI3):7.13 (d, 1H), 7.80 (s, 1H), 7.92 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6775-78-6, its application will become more common.

Reference:
Patent; ALMIRALL,S.A.; GONZALEZ RODRIGUEZ, Jacob; VIDAL JUAN, Bernat; VIDAL GISPERT, Laura; BACH TANA Jordi; WO2012/69202; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, These common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, 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.

Under a nitrogen atmosphere, a 5 L dry and clean four-neck round bottom flask was charged with diisopropylamine (72.8 g, 0.72 mol, 1.06 eq) and 1500 mL of anhydrous tetrahydrofuran, and the temperature was reduced to -70 C.Add n-butyllithium solution (272mL, 2.5M, 0.68mol, 1.0eq), stir to cool to -70 , slowly add D-1 (130g, 0.68mol, 1.0eq) dropwise, and maintain the reaction for 1h after the addition.Slowly add iodine-tetrahydrofuran solution (172g iodine / 300ml THF, 0.68mol, 1.0eq),After the addition, the reaction was maintained for 1 h.The temperature was slowly raised to room temperature, and the reaction was monitored by HPLC for completion.The reaction was quenched with 500 mL of 5% Na2S2O3 solution, and extracted with 2 L of methyl tert-butyl ether.The organic phase was washed with 1500 mL of saturated saline and dried over anhydrous sodium sulfate.Concentrated under reduced pressure to obtain an oil, and recrystallized by adding 600 mL of ethanol.184 g (F-1) of white flaky solid was obtained by filtration,The yield was 85%.

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 108-37-2.

Reference:
Patent; Ningbo Lumilan New Materials Co., Ltd.; Ningbo Dinghao Optoelectric Materials Technology Co., Ltd.; Zhang Yuxiang; Zhang Qingyun; Ding Huanda; Chen Zhikuan; (41 pag.)CN110551154; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6775-78-6, A common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, molecular formula is C6H4ClN3, 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.

478 mg (3.11 mmol) of 6-chloroimidazo[1 ,2-b]pyridazine were introduced into 10 mL of chloroform under argon and, while cooling in ice, 664 mg (3.73 mmol) of N- bromosuccuinimide were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The reaction mixture was then mixed with water and ethyl acetate and, after addition of saturated sodium bicarbonate solution, the phases were separated. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were then washed with saturated sodium chloride solution and dried over sodium sulfate. Sn the final removal of the solvent in vacuo, the desired product was isolated in quantitative yield in the form of an amorphous white solid which was employed without further chromatographic purification in subsequent reactions. 1H-NMR (CHLOROFORM-d): delta [ppm] – 7.12 (d, 1 H); 7.79 (s, 1 H); 7.90, (d, 1 H).

The synthetic route of 6775-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; EIS, Knut; WO2013/87581; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, molecular formula is C8H8Cl2N2, 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. 1127-85-1

General procedure: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

The chemical industry reduces the impact on the environment during synthesis 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

10061-02-6, A common compound: 10061-02-6, name is trans-1,3-Dichloropropene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 1; 382g (406ml) of DMF were initially charged in a Schmizzo and 137g (141 ml) of 1.0 eq. NaOMe (30% solution in methanol) were added. This mixture was then heated to 600C (+ 3C) and 131g (0.753mol) of dimethyl isopropylmalonate were metered in within one hour. Subsequently, a methanol/DMF mixture (201 g) was distilled off under pressure (300 mbar to 60 mbar) and a temperature of 600C. Thereafter, at 800C (+ 30C), 86 g (79 ml, 0.779 mol, 1.03 eq.) of 1 ,3-dichloropropene were metered in within one hour and the reaction mixture was then heated at 800C (+ 3C) for two hours.The reaction mixture was heated to 1400C and a 25% solution of LiCI (0.6 eq.) in methanol (19 g of LiCI in 58 g of methanol) was metered in within two hours, and the reaction mixture was heated at 140-1420C for a further 6 hours, in the course of which a portion of the methanol was distilled off and approx. 1.5 mol of gas (mainly CH3CI and CO2) formed. The maximum amount of gas in the first half hour was approx. 6 liters.On completion of reaction, the solvent (DMF) and the excess methanol were distilled off substantially fully under reduced pressure. The remainder was admixed with 200 g of water, 89 g of 34% HCI and 200 g of MTBE, and the phases were separated. The organic phase was washed 1x with 50 g of water and the solvent was removed under reduced pressure. Approx. 140 g of product were obtained, of which approx. 125 g were ester and 13 g the corresponding acid.To prepare the corresponding acid, the above product was processed further. 140 g of crude product were suspended in 15O g of water and 70 g of 50% NaOH (1.15 eq.) were added. The reaction mixture was initially charged in an autoclave and heated at max. 3 bar and a temperature of 100-1100C for two hours. On completion of reaction, the methanol formed was distilled off via the top. Thereafter, the mixture EPO was adjusted to pH 1.5 with H2SO4 (76%) and extracted 2x with 100 g of IPAT each time, and the solvent was removed under reduced pressure. 125-127 g of acid (96% of theory) were obtained as a colorless liquid; Example 2; A reaction vessel was charged with dimethylformamide (406 ml, 382 g) and sodium methoxide (140 ml, 136 g, 753 mmol, a 30% solution in methanol). The reaction mixture was heated to 600C. Dimethyl isopropylmalonate (127 ml, 131 g, 753 mmol) was metered in within thirty minutes, and methanol was distilled off at a temperature of 69-74C and a pressure of 330-50 mbar. frans-1 ,3-Dichloropropene (70 ml, 84 g, 753 mmol) was metered in at 800C within one hour and the reaction solution was stirred at 8O0C for ninety minutes.CaCb (83.5 g, 753 mmol) was added and the mixture was heated to 140-1450C. Methanol was metered in continuously (a total of 30 ml, 24 g, 742 mmol), in the course of which the reaction temperature was kept at approx. 140-1450C. The suspension is stirred at this temperature for 12 hours, in the course of which gas (mainly CH3CI and CO2) formed. The maximum amount of gas in the first half hour was approx. 6 liters.Dimethylformamide (260 ml, 247 g) was distilled off at 70-800C and a pressure of (150 – 25 mbar). The resulting suspension was cooled to 55C, and admixed with 250 g of water, 90 g of HCI (a 34% aqueous solution) and 190 g of MTBE. The phases were separated and the organic phase was washed with 100 g of water. The organic phase thus obtained was worked up as follows: EPO The organic MTBE phase was concentrated under reduced pressure. The remainder of MTBE was removed by adding 50 g of water and distilling off an MTBE/water mixture.Water (135 g) and sodium hydroxide solution (75 g, 49 ml, a 50% aqueous solution) were added, and the reaction solution was heated at a pressure of max. 3 bar and 105-1100C for two hours. On completion of reaction, approx. 60 ml of an MeOH/water mixture were distilled off. Thereafter, water (135 g) was added and adjusted to pH 3.0-4.0 with H2SO4 (76% aqueous solution). The solution was admixed with isopropyl acetate at 25C and the phases were separated. The organic phase was washed with 30 g of water and the solvent was removed under reduced pressure. 191 g of racemic acid were obtained as brownish liquid (92% of theory).The organic MTBE phase was extracted with water (25 g) and sodium hydroxide solution (10 g, 50% aqueous solution), and then washed with water (25 g). The combined aqueous phases contained 17 g of rac. acid (13% of theory) which can be esterified with MeOH and catalytic amounts of H2SO4.The organic phase was concentrated under reduced pressure and the residue was distilled at 170-1710C and standard pressure. 113 g of rac. ester were obtained as a colorless liquid (79% of theory).

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, trans-1,3-Dichloropropene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DSM FINE CHEMICALS AUSTRIA NFG GMBH & CO KG; WO2007/17018; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

10061-02-6, 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 10061-02-6 as follows.

General procedure: Activated Al2O3 (10 g) was stirred with a solution of 0.56 g (5 mmol) of t-BuOK in 10 mL of tert-butyl alcohol under argon for 20 min. The solvent was removed in a vacuum. To the dry residue was added 0.65 g (5 mmol) of ethyl acetoacetate 1b, the mixture was stirred for 1 h under an argon atmosphere. Then, 0.55 g (5 mmol) of (E)-1,3-dichloropropene 2 was added to the mixture, and the mixture was stirred until the reaction completed (8-10 h, GLC monitoring). The solid was washed with ethyl acetate (150 mL) on as hort column, and the solvent was removed in avacuum. The crude product was purified by column chromatography (SiO2, hexane-ethyl acetate, 9 :1?8 : 2). Yield 0.81 g (79%).

According to the analysis of related databases, trans-1,3-Dichloropropene, the application of this compound in the production field has become more and more popular.

Reference:
Letter; Shakhmaev; Sunagatullina, A. Sh.; Alieva; Zorin; Russian Journal of General Chemistry; vol. 87; 10; (2017); p. 2472 – 2476; Zh. Obshch. Khim.; vol. 87; 10; (2017); p. 1723 – 1727,5;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, 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 13918-92-8, 13918-92-8

Intermediate 36lambda/-[5-Bromo-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide To a cooled (0 0C) solution of 5-bromo-2-(methyloxy)-3-pyridinamine (13.7 g, 67.5 mmol) in pyridine (200 ml) was added slowly 2,4-difluorobenzenesulfonyl chloride (14.37 g, 67.6 mmol) over 15 min (reaction became heterogeneous). The ice bath was removed and the reaction was stirred at ambient temperature for 16 h. Most of the pyridine was removed in vacuo and the residue diluted with water (500 ml). The solids were filtered off and washed with copious amounts of water to give 21 g of crude desired product. More solid appeared in the mother liquor and was filtered and washed with water to give an additional 1.5 g of desired material. The two batches were combined, triturated with DCM (70 ml) and dried in a vacuum oven at 50 0C to give the title compound (15 g). LCMS (Method B) R1 = 1.11 min, MH+ = 378/380.

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, 2,4-Difluorobenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147187; (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. 57946-56-2, name is 4-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., 57946-56-2

EXAMPLE 35 Preparation of N-(4-Chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide STR121 A mixture of 4-chloro-2-fluoroaniline (19.0 g, 130.6 mmol), and 3,4,5,6-tetrahydrophthalic anhydride (19.85 g, 130.6 mmol) in acetic acid (150 mL) is refluxed for 2 hours, treated with additional 4-chloro-2-fluoroaniline (3.0 g), refluxed for 90 minutes, stirred at room temperature overnight and poured into a water/ethyl acetate mixture. The organic phase is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a purple oil. Flash column chromatography of the oil using silica gel and 15% to 20% ethyl acetate in hexanes solutions gives the title product as an off-white solid (25.3 g, mp 81-82 C.).

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:
Patent; American Cyanamid Company; US5726126; (1998); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 15205-15-9, name is 2-Chloro-6-fluorobenzylamine, 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 15205-15-9. 15205-15-9

Step 7: (S) -tert-Butyl (1- (4- ( (2-chloro-6-fluorobenzyl) carbamoyl) -2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) oxazol-5-yl) ethyl) carbamate[0525]To 10 mL of dichloromethane were added (S) -5- (1- ( (tert-butoxycarbonyl) amino) ethyl) -2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) oxazole-4-carboxylic acid (0.3 g, 0.64 mmol) , 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (183.36 mg, 0.96 mmol) and 1-hydroxy-7-azabenzotriazole (130.56 mg, 0.96 mmol) . To the resulting solution were added (2-chloro-6-fluorophenyl) methanamine (0.1 mL, 0.77 mmol) and N, N-diisopropylethylamine (0.33 mL, 1.92 mmol) , and the mixture was stirred at rt for 22 hours. The reaction mixture was washed with water (20 mL ¡Á 3) . The organic layer was dried over anhydrous sodium sulfate. The organic solvent was removed and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 5/1) to give the title compound as a white solid (264 mg, 67) .[0526]1H NMR (400 MHz, CDCl3) : delta ppm 7.59 (dd, J1 8.3 Hz, J2 1.9 Hz, 1H) , 7.54 (d, J 1.8 Hz, 1H) , 7.47 -7.45 (m, 1H) , 7.27 (d, J 4.6 Hz, 1H) , 7.24 (d, J 8.4 Hz, 1H) , 7.10 -7.06 (m, 1H) , 6.71 (t, JF-H 75.0 Hz, 1H) , 5.32 -5.25 (m, 1H) , 4.87 -4.84 (m, 2H) , 3.98 (d, J 6.9 Hz, 2H) , 1.56 (d, J 7.0 Hz, 3H) , 1.45 -1.43 (m, 9H) , 1.38 -1.34 (m, 1H) , 0.73 -0.68 (m, 2H) , 0.44 -0.40 (m, 2H) .

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 2-Chloro-6-fluorobenzylamine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; YU, Tianzhu; ZHANG, Yingjun; ZHANG, Xiangyu; ZHANG, Shiguo; CHENG, Changchung; ZHANG, Jiancun; WO2015/161830; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

39989-43-0, A common compound: 39989-43-0, name is 3,5-Dichlorobenzylamine, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 10 – Synthesis of Compound 10 N-(4-(3,5-dichlorobenzylamino)-2-oxobutyl)-2- naphthamideN-(4-(3,5-dichlorobenzylamino)- 2- oxobutyl) -2-naphthamideTo a solution of 3,5-dichlorobenzylamine (12 mg, 0.068 mmol) in DCM (0.2 mL) was added a solution of 9 (13 mg, 0.054 mmol) in DCM (0.5 mL) at room temperature. The resulting mixture was stirred until all of the 9 had been consumed (within one hr) and then was used straight in the next reaction. MS (ESI) 415 (M+1 ); HPLC fe 6.00 min.

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, 3,5-Dichlorobenzylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MIMETICA PTY LTD; BLASKOVICH, Mark, Arnold, Thomas; CASSIDY, Peter, Joseph; WO2010/96853; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics