Month: June 2021

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

These common heterocyclic compound, 18282-59-2, name is 4-Bromo-1,2-dichlorobenzene, 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. Formula: C6H3BrCl2

Mg (1.93 g, 79.4 mmol) was suspended in Et2O (50 ml). A chip of I2 was added, then heated to 45° C. 3,4-dichlorobenzylchloride (5.50 ml, 39.7 mmol) in Et2O (50 ml) was added slowly and the mixture was stirred at 45° C. for 2 h, then cooled to 23° C. In a second flask, CuCN (71 mg, 0.79 mmol) was suspended in Et2O (20 ml), then cooled to -30° C. under N2. The Grignard reagent was cannulated into the second flask, then warmed to -15° C. Compound 70 (4.75 g, 7.94 mmol) in Et2O (50 mL) was added dropwise. The mixture was stirred at -15° C. overnight, then warmed to 23° C. and stirred for 24 h. The reaction was quenched with 25percent aqueous sodium citrate at 0° C. and the product extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. Purification by silica gel chromatography (eluant: 3percent to 6percent EtOAc:hexane) gave 3.73 g (4.9 mmol, 62percent) of the product 71. MS (M+1): 759.

The synthetic route of 4-Bromo-1,2-dichlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; US2005/182095; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 61881-19-4, These common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, 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.

General procedure: In a typical experimental procedure, a dry, two-necked, 50 mL round-bottomed flask equipped with a nitrogen inlet was charged with 5 mL of dry MeCN, 0.117 g (1.0 mmol) of indole and 0.24 g (1.0 mmol) of NaH. The solution was stirred under a nitrogen atmosphere at room temperature for 30 min, then a solution of 2a (1.0 mmol in 2 mL of dry MeCN) was added dropwise via a syringe. The mixture was stirred at room temperature for 20 h under an N2 atmosphere and then filtered. After removing the solvent under reduced pressure, the crude product was purified by preparative thin-layer chromatography on silica gel [eluent: n-hexane/EtOAC, 4:1] to give the product 4a. The products obtained from indole-3-carbaldehyde were purified by recrystallization from EtOH (twice).

Statistics shows that 2,2,2-Trifluoro-N-phenylacetimidoyl chloride is playing an increasingly important role. we look forward to future research findings about 61881-19-4.

Reference:
Article; Darehkordi, Ali; Rahmani, Fariba; Hashemi, Vahide; Tetrahedron Letters; vol. 54; 35; (2013); p. 4689 – 4692;,
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. 348-59-4, name is 2,5-Dichlorofluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 348-59-4

[ETHYL 4-[(4-HYDROXY-1-PIPERIDINYL)METHYL]-?-PHENYL-1-PIPERIDINEACETATE ] (0.135 g) was dissolved in NMP (3 mL). 1, 4-Dichloro-2-fluorobenzene (0.2 mL) and potassium t- butoxide (56 mg) were added and the solution was heated to [50 C] for 40 h. The solution was cooled to ambient temperature and few drops of aqueous sodium hydroxide solution were added. The mixture was stirred for 60 h, then acetic acid (few drops) was added and the solvent was distilled. The residue was purified by HPLC (0.2% aqueous ammonia: acetonitrile; gradient 95: 5 to 50: 50) to give the title compound (21 mg). MS [[M+H] +] (ES+) 477/479 [IH] NMR [8 (CD30D)] 1.45 (1H, q), 1.68-1. 96 (9H, m), 2.16-2. 21 (2H, m), 2.25-2. 34 (2H, m), 2.57-2. 65 (3H, m), 2.80-2. 93 (2H, m), 4.29-4. 36 [(1H,] m), 4.38-4. 44 [(1H,] m), 6.83 [(1H,] dd), 7.02 (1H, d), 7.23 (1H, d), 7.32-7. 36 (3H, m), 7.44-7. 49 (2H, m)

The synthetic route of 348-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/29041; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics