Author: Jessica.F

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. 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H2ClF3O2S

General procedure: A solution of compound 8 (90 mg, 0.44 mmol), 4-chlorobenzenesulfonyl chloride (103 mg, 0.49 mmol) and triethylamine (68 muL, 0.49 mmol) in dichloromethane (5 mL) was stirred at room temperature for 18 h. The reaction was quenched through the addition of water (20 mL) and the pH adjusted to pH 6-7 using aqueous phosphate buffer solution (0.5 M, pH 7). The mixture was then diluted with dichloromethane (20 mL) and the separated aqueous layer further extracted with dichloromethane (2 x 20 mL). The combined organic layers were washed with aqueous phosphate buffer solution (0.5 M, pH 7) (20 mL), dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. Purification by flash chromatography (dichloromethane/methanol, 40:1) afforded compound 9a as a beige solid (96 mg, 0.25 mmol, 56%).

According to the analysis of related databases, 220227-21-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brimble, Margaret A.; Cook, Gregory M.; Davison, Emma K.; Ferguson, Scott A.; Harbison-Price, Nichaela; Harper, Andrew D.; Heikal, Adam; Jeong, Joo Young; Knottenbelt, Melanie K.; Krittaphol, Woravimol; McConnell, Michelle A.; McGowan, John E.; Mros, Sonya; Rennison, David; Van Zuylen, Essie M.; Walker, Greg F.; Bioorganic and medicinal chemistry letters; (2020);,
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Electric Literature of 1127-85-1, These common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, 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.

Reference Example 39 (S)-1-(2-chloro-5,6,7,8-tetrahydroquinazolin-4-yl)-N-methylpiperidine-3-carboxamide Diisopropylethylamine (3.4 ml, 19.7 mmol) was added into chloroform (25 ml) solution of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (1 g, 4.92 mmol) prepared in Reference Example 33 and (R)-(-)-3-piperidinecarboxylic acid (0.7 g, 5.42 mmol), and then they were stirred at 60 C. for 2 days. After cooling the reaction solution to room temperature, methylamine hydrochloride (0.33 g, 4.92 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.94 g, 4.92 mmol) and 1-hydroxybenzotriazole hydrate (0.67 g, 4.92 mmol) were added thereto, they were stirred at room temperature overnight. The reaction solution was diluted with dichloromethane, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was crystallized by using ether/ethyl acetate to give the titled compound (436 mg) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 6.22 (m, 1H), 3.93 (m, 1H), 3.74 (m, 1H), 3.34 (m, 1H), 3.10 (m, 1H), 2.81 (m, 4H), 2.49 (m, 3H), 1.93-1.84 (m, 4H), 1.70-1.60 (m, 4H).

The synthetic route of 1127-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; SIM, Jae Young; CHA, Myung; KIM, Tae Kyun; YOON, Young Ae; KIM, Dong Hoon; (59 pag.)US2016/90374; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 626-43-7, name is 3,5-Dichloroaniline, 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 626-43-7, Recommanded Product: 3,5-Dichloroaniline

Step 1 Preparation of #-(3,5-dichlorophenyl)-2-hydroxyimino-acetamide To a solution of 3,5-dichloroanilin (10.0 g, 61.7 mmol) in purified water were added conc. hydrochloric acid (12 ml) and 1,4-dioxane (20 ml), and the resulting mixture was heated until it became transparent, followed by the addition of a 50 C. solution of chloral hydrate (10.5 g, 66.9 mmol) and Na2SO4 (66.0 g) in purified water (224 ml) thereto. Then, the resulting mixture was added to a solution of hydroxylamine hydrochloride (13.0 g, 180 mmol) in water (60 ml) and heated for 50 min with flux. After the mixture was cooled to room temperature, the insoluble solid was filtered, washed with distilled water, and dried in a vacuum to afford the title compound as a pale solid (12.8 g, 89%). TLC Rf=0.5 (ethylacetate:n-hexane=1:3); m.p. 196-197 C.; 1H NMR (DMSO-d6) delta 7.39 (t, 1H, J=1.8 Hz, ArH), 7.70 (s, 1H, CHNOH), 7.89 (d, 2H, J=1.8 Hz, ArH), 10.54 (br s, 1H, NH), 12.40 (br s, 1H, NOH); MS (EI) m/e 233 [M+], 216, 202, 189, 161.

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

Reference:
Patent; Korea Research Institute of Chemical Technology; US2009/203708; (2009); A1;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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. name: Cinnamyl chloride

General procedure: A representative procedure of skeleton 4 is as follows: K2CO3 (400 mg, 2.9 mmol) was added to a solution of 3 (1.0 mmol) in acetone (10 mL) at rt. The reaction mixture was stirred at rt for 10 min. Cinnamyl chloride (1.05 mmol) was added to the reaction mixture at rt. The reaction mixture was stirred at reflux for 8 h. The reaction mixture was cooled to rt, concentrated, and extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried, filtered, and evaporated to afford crude product under reduced pressure. Purification on silica gel (hexanes/EtOAc=6:1 to 1:1) afforded 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2687-12-9, its application will become more common.

Reference:
Article; Chang, Meng-Yang; Lu, Yi-Ju; Cheng, Yu-Chieh; Tetrahedron; vol. 71; 8; (2015); p. 1192 – 1201;,
Chloride – Wikipedia,
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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. 303-49-1, name is 3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: chlorides-buliding-blocks

General procedure: In a dried microwave reactor vessel were added 3-bromoquinoline(0.204 mL, 1.5 mmol), Pd(dba)2 (86 mg, 0.15 mmol), K2CO3carbonate (415 mg, 3.00 mmol), S-Phos (185 mg, 0.45 mmol), dryD8-IPA (0.500 mL) and MeCN (1 mL). The mixture was degassedand placed under a nitrogen atmosphere. The sealed reaction tubewas heated to 100 C in a microwave (Biotage Initiator) for 2.5 h.The solvents were removed under reduced pressure, the crudematerial pre-loaded on to silica and purified using flash silica chromatography(15% EtOAc/heptane). The fractions containing thedesired compound were combined and evaporated to dryness toafford 3-deuterioquinoline (140 mg, 72%); 1H NMR (400 MHz,DMSO, 27 C): d (ppm) 7.62 (ddd, J = 1.20, 6.89, 8.11 Hz, 1H), 7.77(ddd, J = 1.50, 6.87, 8.43 Hz, 1H), 7.99 (dd, J = 1.33, 8.18 Hz, 1H),8.03 (d, J = 8.41 Hz, 1H), 8.37 (s, 1H), 8.91 (d, J = 1.70 Hz, 1H); 13CNMR (176 MHz, DMSO, 30 C) 121.0, 126.4, 127.8, 128.0, 128.8,129.3, 135.8, 147.7, 150.3; HRMS (EI): M+, found 130.0643,C9H6DN requires 130.0641.

The synthetic route of 303-49-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Donald, Craig S.; Moss, Thomas A.; Noonan, Gary M.; Roberts, Bryan; Durham, Emma C.; Tetrahedron Letters; vol. 55; 22; (2014); p. 3305 – 3307;,
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Reference of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-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.

[0075] 4-Chloro-3-fluoroaniline (2g, 13.7 mmol) was dissolved in 60 mL of dichloromethane.Under ice bath, saturated sodium bicarbonate solution (60 mL) was added. The mixture wasstirred at 0 C and triphosgene (1.36g, 4.58 mmol) was added. The mixture was stirred at 0 C for1 h and then extracted with dichloromethane and water. The organic layer was dried with sodiumsulfate and filtered. The filtrate solution was concentrated and the residue was treated with 50mL ofhexanes. The hexane solution was concentrated to remove all solvents. The residue wastaken up in 12 mL ofhexanes and filtered. The solution was concentrated and dried to give 1-chloro-2-fluoro-4-isocyanatobenzene as an offwhite solid (1.69 g). 1H NMR (400 MHz,CHLOROFORM-d) 8 ppm 6.82- 6.90 (m, 1 H) 6.93 (dd, J=9.22, 2.65 Hz, 1 H) 7.31 – 7.41 (m, 1H)

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-fluoroaniline, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine, E.; CHEN, Zhi; ERICKSON, Shawn, David; KIM, Kyungjin; LI, Hongju; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter, Michael; YI, Lin; WO2014/56958; (2014); A1;,
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Electric Literature of 627-42-9, 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 627-42-9 as follows.

Step 1. Synthesis of sodium 2-methoxyethanesulfonate A solution of 2-chloroethyl methyl ether (1.01 g, 10.7 mmol) and Na2SO3 (1.42 g, 11.2 mmol) in H2O (5.0 mL) was stirred at reflux for 20 h. The solution was cooled to room temperature and concentrated to give sodium 2-methoxyethanesulfonate (2.33 g, quantitative yield) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 3.53 (t, 2H), 3.37 (s, 3H), 2.70 (t, 2H).

According to the analysis of related databases, 627-42-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; National Health Research Institutes; Ueng, Shau-Hua; Yeh, Shiu-Hwa; Lin, Shu-Yu; Shih, Chuan; (329 pag.)US2017/253569; (2017); A1;,
Chloride – Wikipedia,
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108-37-2, name is 1-Bromo-3-chlorobenzene, 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. Recommanded Product: 108-37-2

General procedure: The substituted aryl bromide (1.0 mmol), 8-hydroxyquinoline (20 mol%) and KOtBu (2.0 mmol) were loaded into a Schlenk tube equipped with a Teflon-coated magnetic stir bar. The unactivated arene (8.0 mL or 80 equiv) was then added and the mixture was stirred at r.t. for 3-5 min. The Schlenk tube was placed in a preheated oil bath at 80 C and the mixture was stirred for 18 h. After completion of the reaction as judged by GC analysis, the Schlenk tube was allowed to cool to r.t. and the contents quenched with H2O and diluted with EtOAc. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel to afford the desired biaryl product.

The synthetic route of 108-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zheng, Xuehua; Wu, Xu-Nian; Chen, Jing-Yi; Luo, Hai-Bin; Wu, Deyan; Wu, Yinuo; Synthesis; vol. 50; 8; (2018); p. 1721 – 1727;,
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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 27139-97-5 as follows. Computed Properties of C7H6BrCl

A 12 mL vial equipped with a magnetic stir bar was charged with 2-bromo-4-chloro methylbenzene (357.3 mg, 1.74 mmol). To this vial was added phenyl boronic acid (233 mg, 1.91 mmol), Pd(OAc)2 (19.5 mg, 0.09 mmol), P(Ph)3 (91.2 mg, 0.35 mmol), and K2 C03 (480 mg, 3.58 mmol). The vial was flushed with nitrogen and evacuated 3 times. A 10:1 mixture of anhydrous THF:H20 was then added by syringe. The resulting mixture was heated at 80 °C for 18 hours. The reaction was then cooled to rt whereupon 5 mL HzO was added. The reaction was extracted with EtOAc (3 x 10 mL) and the combined organic layers were dried over Na2 S04, filtered and concentrated under reduced pressure to yield an oil. The oil was purified using a 12 g ISCO Si02 column eluting with pure hexanes over a 30 minute period. The desired fractions were combinedand concentrated under reduced pressure to yield 5-chloro-2-methyl-1,1′-biphenyl as a clear oil(332 mg, 94percent yield). 1H NMR (400 MHz, Chloroform-d) 8 7.37-7.30 (m, 2H), 7.30-7.24 (m,1H), 7.23-7.18 (m, 2H), 7.16-7.09 (m, 3H), 2.14 (s, 3H).

According to the analysis of related databases, 27139-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; JONES, Todd, K.; CISAR, Justin, S.; GRICE, Cheryl, A.; WANG, Dong-Hui; WEBER, Olivia, D.; WO2015/3002; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, 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 4090-55-5, HPLC of Formula: C5H10ClO3P

Synthesis Example 1 (Synthesis of Phosphorus Compound 1) (Reaction); In a four-necked 1-L flask provided with a stirrer, a thermometer, a dropping device, a hydrochloric-acid-absorber device and a condenser, 104.0 g (1 mole) of neopentyl glycol and 114.4 g of chlorobenzene were fed. The resulting mixture was heated at 45 to 55 C while stirring and 153.5 g (1 mole) of phosphorus oxychloride were dropwise added to the mixture in an hour. After addition, the mixture was heated to 75 C in an hour, and then was allowed to react at the same temperature (75 C) for an hour and 65.7 g of generated hydrogen chloride were recovered. Thereafter, the mixture was depressurized at the same temperature (75 C) and 26.6 kPa for 2 hours and remaining hydrogen chloride was absorbed as a gas. As a result, 298.9 g of the reaction mixture were obtained. The purity of the reaction mixture was found to be 95.6 area % by GPC (gel permeation chromatography). The resulting reaction mixture was cooled to room temperature to which 161.5 g (0.95 mole) of 2-phenylphenol (ortho-phenylphenol), 0.9 g of magnesium chloride and 145.6 g of chlorobenzene were added. The mixture was heated at 65 to 75 C while stirring and 106.1 g (1.05 moles) of triethylamine were dropwise added to the mixture in an hour. Thereafter, the mixture was allowed to react at the same temperature (75 C) for an hour and thereby obtaining a mixture of 5, 5-dimethyl-2-(2′-phenylphenoxy)-1, 3, 2-dioxaphosphorinane-2-oxide.(After-treatment) The obtained mixture was neutralized at 85 C by adding hydrochloric acid solution which corresponds to an excess amount of triethylamine and the mixture was allowed to stand to separate an oil phase. Next, the obtained oil phase was washed with approximately 85 C water and then dehydrated. The obtained oil phase was gradually cooled and 259.8 g of white needle-like crystals were crystallized out from the oil phase. The purity of the obtained crystals was found to be 99.0 area % by GPC. Also, if all of the crystals were assumed to be an object compound, the crude yield was 86.0 %. A structure of the obtained crystals was determined according to results of quantitative analysis of phosphorus by elemental analysis and absorption spectrometry using an UV spectrometer, 1H-NMR, 13C-NMR and FT-IR. The crystals were identified as 5, 5-dimethyl-2-(2′-phenylphenoxy)-1, 3, 2-dioxaphosphorinane-2-oxide (phosphorus compound 1) of the below-mentioned constructional formula. Also, a melting point of the crystal was measured by a microdose melting point apparatus (model number: MP-J3, manufactured by Yanaco Co., Ltd.). Quantitative analysis of phosphorus by elemental analysis and absorption spectrometry (theoretical values in parentheses): Carbon: 64.3 % (64.2 %) Hydrogen: 5.9 % (6.0 %) Phosphorus: 9.7 % (9.7 %) Melting point: 127 to 130 CIR (KBr): 2992, 2352, 1584, 1514, 1485, 1430, 1373, 1306, 1251, 1104, 1158, 1120, 1050, 1004, 980, 947, 922, 877, 701, 624 cm-1 2992, 2352, 1584, 1514, 1485, 1430, 1373, 1306, 1251, 1104, 1158, 1120, 1050, 1004, 980, 947, 922, 877, 701, 624 cm-1 NMR: 1H-NMR (CDCl3; 300MHz); delta 7.71 (1H, d, J=8Hz, o-PP), 7.55-7.26 (8H, m, o-PP), 3.62 (1H, d, J=10Hz, POCH2C(CH3)2-), 3.53 (2H, dd, JHH=10Hz, POCH2C(CH3)2-), 3.48 (1H, d, JHH=10Hz, POCH2C(CH3)2-), 1.17 (3H, s, POCH2C(CH3)2-), 0.42 (3H, s, POCH2C(CH3)2-) ppm1H-NMR (CDCl3; 300MHz); delta 7.71 (1H, d, J=8Hz, o-PP), 7.55-7.26 (8H, m, o-PP), 3.62 (1H, d, J=10Hz, POCH2C(CH3)2-), 3.53 (2H, dd, JHH=10Hz, POCH2C(CH3)2-), 3.48 (1H, d, JHH=10Hz, POCH2C(CH3)2-), 1.17 (3H, s, POCH2C(CH3)2-), 0.42 (3H, s, POCH2C(CH3)2-) ppm13C-NMR (CDCl3; 75MHz); delta 146.9 (d, 2JPC=6Hz), 137.3, 132.7 (d, 3JPC=7Hz), 130.9, 129.6, 129.0, 128.2, 127.6, 125.2, 120.4 (d, 3JPC=2Hz) (o-PP), 77.6 (d, 2JPC=7Hz, POCH2C(CH3)2-), 31.5 (d, 2JPC=6Hz, POCH2C (CH3)2-), 21.6, 19.5 ppm

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, and friends who are interested can also refer to it.

Reference:
Patent; DAIHACHI CHEMICAL INDUSTRY CO., LTD.; EP1925622; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics