Author: Jessica.F

Synthetic Route of 10061-02-6, A common heterocyclic compound, 10061-02-6, name is trans-1,3-Dichloropropene, molecular formula is C3H4Cl2, 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.

Eine geruehrte Loesung von 77,7 ml Diisopropylamin und 200 ml Tetrahydrofuran wird auf -20 C gekuehlt und waehrend 15 Minuten mit 200 ml 2,5 M n-Hexyllithiumloesung (in Hexan) versetzt. Die Loesung wird 15 Minuten bei -20 C nachgeruehrt und anschliessend wird waehrend 30 Minuten eine Loesung von 75,3 ml Isovaleriansaeureethylester in 80 ml Tetrahydrofuran zugetropft. Die Loesung wird 10 Minuten nachgeruehrt und dann waehrend 10 Minuten bei -20 C mit 80 ml DMPU versetzt. Zugabe von 8,2 g Natriumiodid und 19,5 g trans-1,3-Dichlorpropen. Das Reaktionsgemisch wird noch 23 Stunden bei – 20 C nachgeruehrt und anschliessend mit 500 ml 20%-iger waessriger Ammoniumchloridloesung versetzt. Die Mischung wird mit tert.-Butylmethylether (2x 400 ml) extrahiert und die organischen Phasen nacheinander mit 0,1 M Natriumthiosulfatloesung (1x 500 ml), Wasser (1x 500 ml) und Sole (1x 500 ml) gewaschen. Die vereinigten organischen Phasen werden mit 150 g Natriumsulfat getrocknet und eingedampft. Aus dem Rueckstand wird mittels Destillation die Titelverbindung A1 als farbloses Oel erhalten (86,1 g, 84 %). 1H-NMR (400 MHz, CDCl3, delta) : 0,95 (m, 6H), 1,30 (t, 3H), 1,92 (m, 1H), 2,20 – 2,40 (m, 3H), 4,20 (m, 2H), 5, 80 – 6,10 (m, 2H) ppm.

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; Speedel Pharma AG; EP1200384; (2004); B1;,
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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H8ClNO

Step 1(4-Chloro-3-methoxy-phenyl)-methyl-amineIn a 50 mL flask are added 4-Chloro-3-methoxy-phenylamine (907 mg), sodium methoxide (1.56 g), 10 mL anhydrous methanol, and paraformaldehyde (690 mg). Reaction mixture is then stirred overnight at room temperature. Then, paraformaldehyde (173 mg) and sodium methoxyde (311 mg) are added, and reaction mixture is heated at reflux for 1 hour. Sodium borohydride (436 mg) is then added, and reaction mixture is stirred at reflux for 4 hours. Once back at room temperature, mixture is partially evaporated, and KOH aq 1M (50 mL) is then added. The obtained suspension is extracted by Et20, organic phase is dried over Na2S04 and evaporated. The obtained residue is purified by flash chromatography (cHex to cHex/EtOAc 8/2) to give 650 mg of the expected product (66 %).MS [M+H]+ m/z = 171.9 1H-NMR (DMSO- 6) : delta (ppm) 2.66 (d, J = 4.9 Hz, 3H) ; 3.77 (s, 3H) ; 5.80 (q, J = 4.9 Hz, 1H) ; 6.09 (dd, J = 2.5 Hz, J = 8.7 Hz, 1H) ; 6.25 (d, J = 2.4 Hz, 1H) ; 7.04 (d, J = 8.7 Hz, 1H).

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE LILLE 2 DROIT ET SANTE; INSTITUT PASTEUR DE LILLE; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE); CHARTON, Julie; DEPREZ, Benoit; LEROUX, Florence; STAELS, Bart; MUHR-TAILLEUX, Anne; HENNUYER, Nathalie; LESTAVEL, Sophie; LASSALLE, Manuel; DUBANCHET, Barbara; WO2015/189330; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 67952-93-6,Some common heterocyclic compound, 67952-93-6, name is 3-Chloro-4-methylbenzylamine, molecular formula is C8H10ClN, 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.

1,4-Dichlorophthalazine-6-carbonitrile and 3-chloro-4-methylbenzylamine were stirred at room temperature in 1-methyl-2-pyrrolidinone in the presence of DBU, whereby the title compound was obtained as a less polar compound. 1H-NMR (400 MHz, DMSO-d6) delta; 2.29 (3H, s), 4.73 (2H, d, J=5.2 Hz), 7.28-7.32 (2H, m), 7.45 (1H, d, J=0.8 Hz), 8.20 (1H, dd, J=8.4, 0.4 Hz), 8.34 (1H, d, J=8.4, 1.6 Hz), 8.52 (1H, t, J=5.2 Hz), 9.00 (1H, m).

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

Reference:
Patent; Eisai Co., Ltd.; US6498159; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6306-61-2, name is N-(2-Chloroethyl)propan-2-amine 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 6306-61-2, Formula: C5H13Cl2N

To a stirred mixture of 2-methyltetrahydrofuran (1.5L) and KOH (140g, 250mmol) was added water (30ml_). Then intermediate 3 (60g, 166mmol)) andtetrabutylammoniumbromide (13.4g, 41 mmol) were added and the mixture was heated at 50C for 1 hour while stirring. Then N-(2-chloroethyl)-2-propanamine HCI (CAS[6306- 61 -2]) (48g, 299mmol) was added in 1 portion. The mixture was stirred for 18 hours at 50C. When the conversion was complete, water (600ml_) was added to the reaction mixture. The layers were separated and the organic layer was concentrated. The residue was dissolved in 2-propanol (120ml_) and HCI in 2-propanol was added at 60C. After cooling, the HCI-salt was isolated via filtration. After drying at 50C in a vacuum drying oven the HCI-salt was obtained in 83% yield (compound 4a).

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, N-(2-Chloroethyl)propan-2-amine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; SAXTY, Gordon; MURRAY, Christopher William; BERDINI, Valerio; BESONG, Gilbert Ebai; HAMLETT, Christopher Charles Frederick; JOHNSON, Christopher Norbert; WOODHEAD, Steven John; READER, Michael; REES, David Charles; MEVELLEC, Laurence Anne; ANGIBAUD, Patrick Rene; FREYNE, Eddy Jean Edgard; GOVAERTS, Tom Cornelis Hortense; WEERTS, Johan Erwin Edmond; PERERA, Timothy Pietro Suren; GILISSEN, Ronaldus Arnodus Hendrika Joseph; WROBLOWSKI, Berthold; LACRAMPE, Jean Fernand Armand; PAPANIKOS, Alexandra; QUEROLLE, Oliver Alexis Georges; PASQUIER, Elisabeth Therese Jeanne; PILATTE, Isabelle Noelle Constance; BONNET, Pascal Ghislain Andre; EMBRECHTS, Werner Constant Johan; AKKARI, Rhalid; MEERPOEL, Lieven; WO2011/135376; (2011); 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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1996-29-8

General procedure: In a 15 mL sealed tube equipped with a magnetic stirring bar were added 1 (1 mmol),2 (0.8 mmol), tert-butyl isocyanide (1.2 mmol, 136 muL), Pd(OAc)2 (0.03 mmol, 7 mg),DPEPhos (0.06 mmol, 32 mg), Cs2CO3 (0.8 mmol, 261 mg), and anhydrous DMF (2.0mL). The tube was purged with argon, and the contents were stirred at 100 C for 2 h.Then Na2S*9H2O (1.2 mmol, 240 mg) was added for 2 h. After reaction completion,the mixture was filtered through a pad of Celite, and DMF was removed by a vacuum.The combined filtrates were refluxed in THF (15 mL) and oxalic acid (1 M, 3 mL) for 8h. The solvents were removed under reduced pressure, then poured into brine (20mL) and extracted by ethyl acetate (3 × 30 mL). The combined organic layers weredried (Na2SO4) and evaporated. The residue was purified on a silica gel column usingpetroleum ether/ethyl acetate as the eluent to give the pure target product.

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; Zhang, Fang-Ling; Chen, Zhen-Bang; Liu, Kui; Yuan, Qing; Jiang, Qing; Zhu, Yong-Ming; Synlett; vol. 29; 5; (2018); p. 621 – 626;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2613-34-5, name is 3-Chloro-2,4-difluoroaniline, 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: 3-Chloro-2,4-difluoroaniline

Et3N (0.19 mL, 1.35 mmol) was added to 3-fluoro-1-methyl-4-[[(1R)-2,2,2-trifluoro-1-methyl-ethyl]sulfamoyl]pyrrole-2-carboxylic acid (146 mg, 0.46 mmol), HATU (218 mg, 0.57 mmol)2,4-difluoroaniline (119.8 mg, 0.92 mmol) in DMF (1 mL, 12.92 mmol) and stirred at 65Covernight. The solution was directly charged on a silica gel column and purified by column chromatography using a gradient from 10 till 100% EtOAc in heptane. The product fractions were concentrated and the residue was crystallised from methanol (10 mL) upon addition of water. The white crystals were filtered off and dried at 50C overnight, resulting in compound 312 (105 mg). Method D: Rt: 1.88 mm mlz: 428.0 (M-H) Exact mass: 429.1. Differentialscanning calorimetry: From 30 to 300 C at 10C/mm: peak at 179.4C.?H NMR (400 MHz, DMSO-d6) oe ppm 1.18 (d, J=7.0 Hz, 3 H), 3.81 (s, 3 H), 3.91 – 4.03 (m, 1 H), 7.07 – 7.14 (m, 1 H), 7.31 – 7.39 (m, 1 H), 7.54 (d, J=4.6 Hz, 1 H), 7.63 – 7.72 (m, 1 H), 8.59 (d, J=8.8 Hz, 1 H), 9.69 (s, 1 H).

The synthetic route of 2613-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1435-44-5,Some common heterocyclic compound, 1435-44-5, name is 1-Chloro-2,4-difluorobenzene, molecular formula is C6H3ClF2, 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.

(3-Chloro-2,6-difluoro-phenyl)-methanol (G=Cl, G’=H. G”=F) The title compound was prepared from 1-chloro-2,4-difluoro-benzene by a procedure analogous to that for (2,6-difluoro-4-methyl-phenyl)-methanol, above. 1H NMR (400 MHz, CDCl3) delta1.90 (t, J=6.4 Hz, 1H), 4.78 (d, J=6.4 Hz, 2H), 6.87 (app. dt, J=1.8, 8.9 Hz, 1H), 7.32 (app. dt, J=5.8, 2.8 Hz, 1H) ppm.

The synthetic route of 1435-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US6235764; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1005-56-7, A common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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.

6b (100 mg, 0.30 mmol) was dissolved in 5 mL of acetonitrile,4-Dimethylaminopyridine (162 mg, 1.33 mmol) andThiocarbazoformate (0.1 mL),After stirring at 0-60 C for 2-12 hours, the reaction solution was filtered,Concentrated, separated by column (n-hexane / ethyl acetate: 20/1)To give colorless oil 9 (122 mg, 0.26 mmol, 86%).

The synthetic route of 1005-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Xie Weijia; Zhang Chenxi; Wang Zihao; Wu Xiaoming; Xu Jinyi; Yao Hequan; Lin Aijun; (12 pag.)CN107043403; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route 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.

To a suspension of 4-chloro-3-fluoroaniline (10.67 g, 73.3 mmol) and Na2CO3 (24.5 g, 125 mmol) in Et20 (300 ml) at -10 C under N2 was added TFAA (12.23 ml, 88 mmol) dropwise. The mixture was allowed to warm to rt for 18 h. The reaction mixturewas diluted with hexane (300 ml), and filtered. The filtrate was washed with ice-water,10% aq NaHCO3, and brine, dried over Na2SO4, and concentrated. A pale yellow solid obtained as N-(4-chloro-3-fluorophenyl)-2,2,2-trifluoroacetamide (17 g, 96 % yield). MS (ESI) m/z: 242.1 (M+H)t

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; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; PINTO, Donald J. P.; CORTE, James R.; EWING, William R.; (163 pag.)WO2016/205482; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1940-29-0, 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. 1940-29-0 name is 4-Bromo-3,5-dichloroaniline, 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.

(4-Bromo-3,5-dichloro-phenyl)-[5-methanesulfonyl-2-(4-methoxy-benzyl)-2H- [l,2,4]triazol-3-yl]-amine In a 25 mL round bottle, 5-chloro-l-(4-methoxybenzyl)-3-(methylsulfonyl)-lH-l,2,4-triazole (200 mg, 663 muiotaetaomicron, Eq: 1.00) was combined with DMF (3 mL) to give a colorless solution. 4- Bromo-3,5-dichloroaniline (160 mg, 663 muiotaetaomicron, Eq: 1.00) and sodium 2-methylpropan-2-olate (127 mg, 1.33 mmol, Eq: 2.00) were added. The reaction was degassed by nitrogen for 5 min. The resulting solution was heated to 85 C overnight under nitrogen. The reaction mixture was cooled and diluted with 20 mL H20, added Ether (30×2 mL) to extract the product, dried the organic layer over anhydrous Na2S04, concentrate the solution, purify the compound by column (Hexanes/EtOAc = 70/30) to afford the compound 180mg (54%). MH+ 507.0

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3,5-dichloroaniline, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DING, Qingjie; JIANG, Nan; WEIKERT, Robert James; WO2014/135472; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics