Tag: M.W=100-200

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 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

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

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

Synthetic Route of 2845-89-8,Some common heterocyclic compound, 2845-89-8, name is 1-Chloro-3-methoxybenzene, molecular formula is C7H7ClO, 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: Under N2 atmosphere, KOtBu (1.3 equiv), toluene (1.0 mL), amines 5 (0.84 mmol), aryl chlorides 4 (0.7 mmol) and finally a solution of complex 3a (20-100muL, 0.01-0.05 mol%, prepared from 0.014 mmol 3a in 4.0mL toluene) were successively added into a Schlenk reaction tube. The mixture was stirred vigorously at 110 C for 24h. Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (SiO2) to give the corresponding products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloro-3-methoxybenzene, its application will become more common.

Reference:
Article; Liu, Feng; Hu, Yuan-Yuan; Li, Di; Zhou, Quan; Lu, Jian-Mei; Tetrahedron; vol. 74; 39; (2018); p. 5683 – 5690;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 104-11-0, 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. 104-11-0 name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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.

General procedure: A solution of 0.17g (1.40mmol) of N-benzylmethylamine, 0.20g (1.40mmol) of K2CO3 and 0.40g of (R,S)-3(4-bromobutyl)-5-phenyloxazolidin-2-one 23 in ACN was allowed to stirring under reflux for 6-12h and monitored by TLC until the reaction was completed. The hot solution was filtered and concentrated in vacuo to afford 0.29g (85.0mmol) of a chromatography pure yellow oil 2a.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Chlorophenyl)-N-methylmethanamine, and friends who are interested can also refer to it.

Reference:
Article; Zampieri, Daniele; Vio, Luciano; Fermeglia, Maurizio; Pricl, Sabrina; Wuensch, Bernhard; Schepmann, Dirk; Romano, Maurizio; Mamolo, Maria Grazia; Laurini, Erik; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 712 – 726;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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 4584-46-7, Safety of 2-Chloro-N,N-dimethylethanamine hydrochloride

The experimental equipment used in this study was a Vapourtec R4/R2+ flow reactor. Stock A: Ginkgolide B (4.4g), acetonitrile (100mL). Stock B: DECH (2.15g), potassium iodide (0.332g), acetonitrile (90mL), water (10mL). Initially, two flows were pumped into micromixer LH 25. Upon mixing together, the mixture entered the packed bed microreactor filled with acid-binding agents. The total volume of the packed bed microreactor was 24.5mL. However, the remaining volume was 4.5mL when the microreactor was filled with calcium carbonate (2.5g). The volumetric flow rate of stock A/B was 0.75mL/min. That is to say, the residence time in the microreactor was 3min. Upon completion at a set temperature for the appropriate residence time, the obtained organic layer was concentrated under vacuum and further purified by column chromatography on silica gel (MeOH/CH2Cl2=1:50). Dimethylaminoethyl ginkgolide B: 1H NMR (DMSO-d6, 300MHz): delta 7.12 (s, 1H), 6.32 (s, 1H), 6.12 (s, 1H), 5.31 (d, 1H, J=3.6Hz), 5.12 (s, 1H), 4.54 (d, 1H, J=7.5Hz), 4.35-4.41 (m, 1H), 4.07 (d, 1H, J=7.2Hz), 3.55-3.59 (m, 1H), 2.81-2.88 (m, 1H), 2.57-2.64 (m, 1H), 2.32 (d, 1H, J=12.6Hz), 2.18 (s, 6H), 2.11-2.12 (m, 1H), 1.83-1.94 (m, 1H), 1.71-1.77 (m, 1H), 1.11 (d, 3H, J=6.9Hz), 1.04 (m, 9H). 13C NMR (DMSO-d6, 300MHz): delta 176.44, 173.02, 170.18, 109.59, 98.40, 92.78, 82.00, 78.62, 74.36, 74.00, 72.19, 67.52, 64.11, 57.44, 48.64, 43.71, 41.62, 40.09, 39.81, 39.53, 39.25, 38.98, 36.57, 31.75, 28.58. HRMS calcd. for C24H33NO10 496.2177 [M+H], found 496.2196.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Qin, Yin-Lin; He, Wei; Su, Mei; Fang, Zheng; Ouyang, Ping-Kai; Guo, Kai; Chinese Chemical Letters; vol. 27; 10; (2016); p. 1644 – 1648;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2613-32-3, name is 2-Chloro-4,5-difluoroaniline, molecular formula is C6H4ClF2N, 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. Safety of 2-Chloro-4,5-difluoroaniline

Lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (42 ml, 1 M solution in tetrahydrofuran, 42 mmol, CAS No 4039-32-1 ) was added drop wise within 5 minutes to a solution of 2-chloro-4,5-difluoroaniline (3.88 g, 23.2 mmol) in tetrahydrofuran (1 10 ml) at -78 C and the mixture was stirred for 1 h at that temperature. A solution of ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}-1-(2-chloroethyl)cyclohexanecarboxylate (10.0 g, 21 .1 mmol) in tetrahydrofuran (1 10 ml) was added and the mixture was stirred for 2 h at -78(C. The mix ture was warmed to room temperature and stirred for 4 d. For work-up, the reaction mixture was added to a mixture of water and sodium bicarbonate solution and the mixture was extracted with ethyl acetate (3x). The combined organic phases were washed with sodium chloride, dried over sodium sulfate and concentrated under reduced pressure, the residue was purified by flash chromatography (340 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 25% ethyl acetate). The product containing fractions were concentrated and were purified a second time by flash chromatography (120 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 25% ethyl acetate) to give the title compound in 2 fractions: fraction 1 (7.53 g, single isomer based on1H NMR, isomer 1, contains impurities from aniline and isomer 2), fraction 2 (1 .13 g, isomer 2). Fraction 1 (isomer 1 ):1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 7.67-7.55 (m, 5H), 7.52-7.30 (m, 9H), 3.97 (br s, 1H), 3.60 (t, 2H), 2.15-2.07 (m, 2H), 2.04 (t, 2H), 1 .76-1 .63 (m, 2H), 1 .58-1 .45 (m, 2H), 1 .39-1 .27 (m, 2H), 1 .05 (s, 9H). LC-MS (Method 1 ): Rt= 1 .80 min; MS (ESIpos): m/z 518.3 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2613-32-3, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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. Computed Properties of C4H8BrCl

Example (C):1Preparation of 7-(4-cMorobutoxy)-3,4-dihydro carbostyril (III):; The three necked flask was charged with 7-hydroxy-3, 4-dihydro carbostyril (II) (50gm, 0.306moles) in acetone: water mixture (400ml: 25ml). To this mixture was successively added potassium carbonate (50,8gm, 0,367moles), PEG-400 (61.2gm) and stirred at ambient temperature for one hour. The l-bromo-4-chlorobutane (157ml, 0.918moles) was added to mixture over a period of 10 min. Reaction mixture was then stirred at ambient temperature for 15-16 hours. The progress of the reaction was monitored by TLC (eluent: chloroform: methanol (90:10)). Reaction mixture was filtered and the inorganics were washed with acetone (100ml). The solvent was removed under the reduced pressure below 40 0C. The thick oily residue obtained was stirred with n-hexane (500ml) and water (500ml), at 10-15 0C, for a period of 45 min.The solid was filtered, washed with water (500ml) and then with n-hexane (500ml). The resulting solid was dried at 65-70 0C to obtain 7-(4-chlorobutoxy)-3, 4-dihydro carbostyril (III) (72.7gm, 94 %).1H (CDCl3): 1.9 (m, 4H), 2.5 (m, 2H), 2.8 (m, 2H), 3.6 (m, 2H), 3.9 (m, 2H), 6.3 (s, IH), 6.4 (d, IH), 7.0 (d, IH) and 9.3 (s, IH)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6940-78-9, its application will become more common.

Reference:
Patent; UNICHEM LABORATORIES LIMITED; WO2007/94009; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics