Month: August 2021

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. 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Product Details of 7051-16-3

General procedure: To a solution of 4-bromoanisole (200.8 mg, 1.09 mmol, 1.0 equiv) in acetonitrile (2 mL) was added N-chlorosuccinimide(NCS) (158.3 mg, 1.19 mmol, 1.1 equiv) at rt to give a slightly cloudy mixture. Chlorotrimethylsilane (TMSCl) (14 muL, 0.11 mmol, 0.1 equiv) was then added drop-wise to the reaction mixture. Within a few minutes, the reaction mixture became clear pale yellow solution. The mixture continued to stir at rt for 1 h and was diluted with hexane. The biphasic mixture was concentrated on a rotary evaporator to a crude white solid-oil mixture. This mixture was taken up in hexane and filtered through a short plug of SiO2 and eluted with 5-10% EtOAc-hexane solution. The clear filtrate was concentrated to obtain a mixture of 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl) 237.0 mg (88% of 2a-Cl and 11% of 2a-diCl,based on NMR ratio 2a-Cl: 2a-diCl = 7.1: 1.0; as a pale yellow solid).

The synthetic route of 7051-16-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maibunkaew, Tapanee; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Bunrit, Anon; Ruchirawat, Somsak; Synlett; vol. 25; 12; (2014); p. 1769 – 1775;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 104-11-0

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.

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 104-11-0.

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

Reference of 626-43-7, A common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, 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.

To a solution of 3,5-dichloroaniline (3.56 g, 21.97 mmol) in acetonitrile (60 mL) at 0C was added NBS (4.30 g, 24.17 mmol). The reaction was kept at 0C and stirred for 3 h. The solvent was concentrated under reduced pressure and the residue was partitioned between EtOAc (200 mL) and water (100 mL). The organic layer was washed with brine, dried over MgS04, filtered and concentrated in vacuo. The residue was purified by chromatography on silica (Eluant: Hexane:EtOAc = 90: 10) to afford the title compound 4-bromo-3,5-dichloroaniline. LCMS calc. = 239.89; found = 239.84/241.84 (M+H)+. NMR (500 MHz, CDC13): delta 7.71 (s, 2 H); 3.80-

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; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; ZHANG, Ting; CHEN, Yi-Heng; GUO, Liangqin; HRUZA, Alan; JIAN, Tianying; LI, Bing; MENG, Dongfang; PARKER, Dann, L., Jr.; SHERER, Edward, C.; WOOD, Harold, B.; SAKURADA, Isao; (130 pag.)WO2016/94260; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 101-79-1,Some common heterocyclic compound, 101-79-1, name is 4-(4-Chlorophenoxy)aniline, molecular formula is C12H10ClNO, 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.

B. r4- (4-Chloro-phenoxy)-phenylaminol-acetic acid ethyl ester. Oxo-acetic acid ethyl ester (0.243 g, 2.38 mmol) was added to a solution of 4- (4-chloro- phenoxy)-phenylamine (0.5 g, 2.27 mmol) in DCE (48 mL). The mixture was stirred at rt for 15-20 min, before the addition of Na (OAc) 3BH (0.625 g, 2.95 mmol) and AcOH (0.24 mL). The mixture was stirred at rt for 5 h. More oxo- acetic acid ethyl ester (0.08 g) and AcOH (0.03 mL) were added, and the mixture was stirred at rt overnight. Saturated NaHCO3 (50 mL) and excess CH2CI2 (50 mL) were then added to the reaction mixture. The aqueous layer was extracted with CH2CI2 (3 X 50 mL). The combined organic layers were washed with brine (40 mL) and dried (MgS04), and the solvent was removed. Purification by column chromatography with 20-50percent EtOAc/hexanes afforded 0.4 g (61 percent) of the desired product. MS (electrospray) : mass calculated for Ct4H12CINO3, 305.76 ; m/z found, 306.1 [M+H] +.’H NMR (400 MHz, CDCI3) : 7.25-7. 23 (m, 2H), 6.93-6. 86 (m, 4H), 6.64-6. 62 (m, 2H), 4.28 (dd, J= 14.3, 7.1 Hz, 2H), 3.92 (s, 2H), 1.33 (t, J= 7.1 Hz, 3H).

The synthetic route of 101-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2005/44810; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

Step C: Synthesis of (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-methyl-amine. To a solution of 2,4-dichloro-5,6,7,8-tetrahydro-quinazolin (8.70 g, 42.8 mmol) in THF (87 mL) was added 40% aqueous MeNH2 (8.32 g, 107 mmol). The mixture was stirred at ambient temperature for 8 hr. The solution was poured into saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated, and purified by flash chromatography (NH-silica, 50% EtOAc in hexane) to give (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-methyl-amine (7.04 g, 83%) as a white solid. ESI MS m/e 220, M + Na+; 1H NMR (300 MHz, CDCl3) delta 1.74-1.92 (m, 4 H), 2.26 (t, J= 5.5 Hz, 2 H), 2.67 (t, J= 5.6 Hz, 2 H), 3.05 (d, J= 5.0 Hz, 3 H), 4.81 (s, 1 H).

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; Taisho Pharmaceutical Co. Ltd.; Arena Pharmaceuticals, Inc.; EP1464335; (2004); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 367-22-6, 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. 367-22-6 name is 4-Chloro-3-fluoroaniline, 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.

At 0 C, to a mixture of 4-chloro-3-fluoroaniline (7 g, 48.1 mmol) in DCM (100 mL) was added pyridine (7.8 mL, 96 mmol), followed by phenyl carbonochloridate (6.3 mL, 50.5 mmol). The mixture was stirred at 0 C for 1 h, then warmed up to rt overnight. The mixture was washed with IN HCl and back extracted with DCM. The combined organics were washed with brine, dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give phenyl (4-chloro-3-fluorophenyl)carbamate (12 g, 45.2 mmol, 94 % yield) as a colorless solid. The crude product was used without further purification.LC/MS (ESI): m/z 266.1 (M+H)+, 1.13 min (ret. time).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BAILEY, James; CHEN, Yao; HURLE, Mark; LEACH, Craig; TURUNEN, Brandon; (103 pag.)WO2018/134731; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 6940-78-9,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.

Preparation of 4-Methyl-l,2,4-triazine-3,5(2H,4H)-dione2-Acetyl-l,2,4-triazine-3,5(2H,4H)-dione (10 g, 64.5 mmol) was added portionwise over 40 min to a suspension of sodium hydride (3.09 g, 60wt suspension in oil, 77.4 mmol) in DMF (160 mL) and stirred vigorously for 45 min. Iodomethane (4.41 mL, 10.1 g, 70.9 mmol) was added and the whole mixture stirred at ambient temperature for 66 h under a dry nitrogen atmosphere. A slight ppt remained but this disappeared on warming to evaporate the solvent. The residue was dissolved in EtOH (200 mL) and /rara-toluenesulfonic acid monohydrate (1.4 g, -10 mol ) was added and the yellow solution refluxed for 2 h before allowing to cool. Solvent was evaporated and toluene (275 mL) added with heating. After standing overnight, solid was filtered off. The crude solid was suspended in EtOAc (250 mL) and stirred overnight to dissolve out sodium iodide, then filtered off to give 4-methyl-l,2,4-triazine-3,5(2H,4H)-dione (4.9 g, 60%).1H NMR (300 MHz, DMSO-d6) 5 3.10 (3H, s, CH3), and 7.48 (lH, s, CH). 13C NMR (75 MHz, DMSO-d6) delta 25.6 (CH3), 134.4 (CH), 149.4 (NHC(=0)CH), and 156.5 (NHC(=0)NH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-chlorobutane, its application will become more common.

Reference:
Patent; GE HEALTHCARE LIMITED; MEDI-PHYSICS, INC.; NEWINGTON, Ian, Martin; WYNN, Duncan George; NAIRNE, Robert James Domett; GUILBERT, Benedicte; MANDAL, Subrata; JINTO, Jose; VARADARAJAN, Sunderaraman; RANGASWAMY, Chitralekha; BETTS, Helen; DAVIS, Rebecca; WO2011/150183; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 870-24-6, 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. 870-24-6, name is 2-Chloroethanamine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A stirred solution of 2-chloroethylamine hydrochloride (l.OOg, 8.62mmol) and Et3N (3.60ml, 25.9mmol) in dry DCM (25ml) at 0C was treated with a solution of nosyl chloride (1.91g, 8.62mmol) in dry DCM (25ml) dropwise. On complete addition, the solution was warmed to ambient temperature and stirred overnight. The solution was evaporated and the residue purified by column chromatography (Si02, 20% EtOAc to 30% EtOAc in cyclohexane) to afford the title compound as a white solid (2.03g, 89%). XH NM (400 MHz, DMSO-d6) delta 8.45 – 8.38 (m, 3H), 8.09 – 8.04 (m, 2H), 3.59 (t, J = 6.0 Hz, 2H), 3.17 (s, 2H).

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-Chloroethanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AB SCIENCE; BENJAHAD, Abdellah; MARTIN, Jason; SCHALON, Claire; PEZ, Didier; CHEVENIER, Emmanuel; SANDRINELLI, Franck; PICOUL, Willy; MOUSSY, Alain; WO2015/144614; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 62356-27-8 as follows. name: 1-Bromo-3-chloro-2-methylbenzene

EXAMPLE 175 6-(3-chloro-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 275, Structure 4 of Scheme II, where R1 =3-chloro-2-methylphenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (70.0 mg, 0.22 mmol) and 2-bromo-6-chlorotoluene (45.2 mg, 0.22 mmol). The crude material was purified by flash column chromatography (75 ml silica, hexane to 5% ethyl acetate/hexane) to afford 63.1 mg (96%) of Compound 275. Data for Compound 275: 1 H NMR (400 MHz, acetone-d6) 7.30 (d, J=8.3, 1 H), 7.16 (m, 1 H), 6.95 (s, 1 H), 6.87 (d, J=10.2, 1 H), 6.54 (d, J=8.0, 1 H), 5.36 (s, 1 H), 5.25 (s, 1 H), 2.03 (s, 3 H), 1.28 (s, 6 H).

According to the analysis of related databases, 62356-27-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1939-99-7, 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. 1939-99-7, name is Phenylmethanesulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

K2CO3 (8.7 g, 62 mmol) was added into a mixture of phenylmethanesulfonyl chloride (6 g, 31 mmol) and 2-bromoethanamine hydrobromide (6.4 g, 31 mmol) in DCM (100 mL) at 0 C. And the resulting mixture was stirred at r.t. for 4 hours and left standing overnight. Upon the completion of reaction, water (100 mL) was added in and DCM phase was separated. The aqueous phase was extracted with DCM. The combined organic phase was dried over Na2SO4, filtered and concentrated in vacuo to provide a crude which was separated with column chromatography (silica gel with 200-300 mesh, 0 to 50% of EtOAc in petroleum ether) to provide compound N-(2-bromoethyl)(phenyl)methanesulfonamide (7.0 g, 80%) as a pale yellow solid. 1H NMR (300 MHz, CDCl3) delta 7.40 (m, 5H), 4.58 (m, 1H), 4.29 (s, 2H), 3.34-3.29 (m, 4H). LCMS (ESI), 300, 302 [M+Na]+, Br pattern found.

The chemical industry reduces the impact on the environment during synthesis Phenylmethanesulfonyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Genentech, Inc.; Fauber, Benjamin; Gobbi, Alberto; Rene, Olivier; van Niel, Monique Bodil; Gancia, Emanuela; Gaines, Simon; Ladduwahetty, Tammy; Vesey, David; Ward, Stuart; Winship, Paul; (101 pag.)US2016/168141; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics