Tag: M.W=100-200

Application of 694-80-4, A common heterocyclic compound, 694-80-4, name is 1-Bromo-2-chlorobenzene, molecular formula is C6H4BrCl, 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.

III – 1 raw materials (0.5g, 2 . 6mmol) dissolved in 42 ml in the mixed solvent (toluene/ethanol/water, 3:1: 3, v/v/v), adding raw material III – 2 (0.3g, 2 . 6mmol), triphenyl phosphorus palladium (0.15g, 0 . 13mmol), anhydrous sodium carbonate (0.69g, 6 . 5mmol), under the protection of nitrogen, 60 C heating reaction 24h. After the reaction cooled to room temperature, water 20 ml dilution, diatomite groundwork for filtering, ethyl acetate (15 ml ¡Á 3) washing the filter cake, the filtrate with ethyl acetate (30 ml ¡Á 4) extraction, the combined organic phase to saturated NaCl solution (20 ml ¡Á 2) washing, to obtained organic phase dried with anhydrous sodium sulfate, filtered, filtrate is decompressed and evaporate the solvent, the residue by column chromatography (petroleum ether/ethyl acetate, 70:30, v/v) to obtain the gray solid 0.47g, yield 84%.

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; China Pharmaceutical University; Huang Wenlong; Qian Hai; Liu Chunxia; (26 pag.)CN106748922; (2017); A;,
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. 1939-99-7, name is Phenylmethanesulfonyl chloride, A new synthetic method of this compound is introduced below., Computed Properties of C7H7ClO2S

Collidine (0.59 mL, 4.5 mmole) was added in one portion to a stirred solution of the compound of Example 94 (0.89 g, 3.7 mmole) and benzylsulfonyl chloride (0.86 g, 4.5 mmole) in acetonitrile (20 ml) cooled in an ice bath. The solution was stirred for 5 minutes at 0 C., followed by 45 minutes at room temperature. The reaction mixture was quenched with water, then diluted with ethyl acetate (100 mL), washed with 3% HCl (until aqueous layer was pH 1), and brine, dried over magnesium sulfate, and the solvent was removed. The residue was dissolved in methanol, concentrated to a volume of approximately 3 mL, and the product was precipitated with the addition of diethyl ether. The precipitate was filtered to give 0.67 g of the title compound. The filtrate was concentrated and chromatographed on flash silica gel using 20 to 67% ethyl acetate hexanes as eluent. An additional 0.20 g of the title compound was recovered. A total of 0.87 g of the title compound (59% yield) was recovered. Rf=0.29 (silica gel, 33% ethyl acetate/hexanes).

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; Corvas International, Inc.; US6342504; (2002); 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. 10272-06-7, name is 3-Chloro-5-methoxyaniline, A new synthetic method of this compound is introduced below., Safety of 3-Chloro-5-methoxyaniline

To a solution of compound obtained from Step c (0.1 g, 0.3003 mmoles) in 7V,7V- dimethylformamide (1 ml) were added 1 -hydroxy benzotriazole (0.04 g, 0.3003 mmoles), N-ethyldiisopropyl amine (0.116 g, 0.9009 mmoles) and 3-chloro-5-methoxyaniline (0.047 g, 0.3003 mmoles) at room temperature. The reaction mixture was allowed to stir at room temperature for about 5 minutes and then l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.086 g, 0.4505 mmoles) was added to it. The reaction mixture was again stirred at room temperature for about 12 hours. After completion, the solvent was evaporated under vacuum, diluted with water and extracted with ethyl acetate. The resulting organic layer was washed with water, dried over anhydrous sodium sulphate, filtered and evaporated under vacuum to afford an oily residue which was purified through flash column chromatography eluting with ethyl acetate :dichloromethane (3:7) to afford the title compound as white solid. Yield: 0.07g.1H NMR (400 MHz, DMSO-i? delta: 9.48 (s, 1H), 7.82 – 7.88 (m, 2H), 7.37 – 7.44 (m, 2H), 7.28 – 7.34 (m, 2H), 7.18 – 7.24 (m, 1H), 7.15 (d, J= 13.64 Hz, 1H), 7.10 (d, J= 8.08 Hz, 2H), 4.91 (s, 2H), 3.82 (s, 3H), 3.07 (s, 3H), 2.17 (s, 3H), 2.15 (s, 3H ).Mass spectrum (m/z, +ve ion mode): 472 [M++l], 474 [M++l+2].

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; RANBAXY LABORATORIES LIMITED; VERMA, Ashwani Kumar; MALHOTRA, Sanjay; GHORPADE, Satish Madhav; DAWANGE, Mahesh Balasaheb; RAY, Abhijit; GUPTA, Suman; SRIVASTAVA, Punit; DASTIDAR, Sunanda Ghosh; WO2012/14127; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 6940-78-9, A common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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.

[0096] A mixture of beta-naphthol (1gm, 0.006 mole), anhydrous K2CO3 (10 gm, in excess) and 1-bromo 4-chlorobutane (0.8 ml, 0.006 mole) was refluxed in dry acetone (50 ml) for 6 hours. Reaction mixture was filtered and filtrate was concentrated to get oily compound, which was crystallized with benzene-hexane to give the colorless crystals of pure desired compound, m.p. 112 C., (yield 1.6 gm, 98%).

The synthetic route of 6940-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; US2004/192688; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 72934-36-2, name is 1-(4-Chlorophenyl)cyclopropanamine, 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 72934-36-2, Recommanded Product: 72934-36-2

To a stirred solution of 1 -benzyl 3 -((3aR ,5aR ,5bR ,7aR ,95, 11 aR, 1 ibR, 1 3a5)-3a-iso cyanato- 1 -isopropyl-5a,5b,8,8, 11 a-pentamethyl-2-oxo-3 ,3a,4,5,5a,5b,6,7,7a,8,9, 10,11,11 a, 1 ib, 12,13,1 3a-octadecahydro-2H-cyclopenta[ajchrysen-9-yl) (1R,35)-2,2-dimethylcyclo butane-i,3-dicarboxylate (Intennediate-2, 3.0 g, 4.213 mmol, 1.0 eq) in THF (30 ml) wasadded DIPEA (2.16 ml, 12.64 mmol, 3.0 eq) followed by i-(4-chlorophenyl)cyclopropan-i- amine (Intennediate-4, 0.847 g, 5.056 mmol, 1.2 eq). The reaction mixture was stirred at room temperature for about 16 hours. TLC indicated starting material was consumed and the desired product was observed. The reaction mixture was diluted with water (75 ml) andextracted with ethyl acetate (3×75 ml). The combined organic extracts were washed with water (75 ml) and brine solution (50 ml). The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silicagel column chromatography by using 0-2% methanol in dichloromethane gradient. The fractionscontaining the expected product were combined and concentrated under reduced pressure to give the desired product (3.0 g, 80.9% yield) as a white solid. ?H NMR (300 MHz, CDC13): ppm 7.37-7.34 (m, 5H), 7.30 (d, J = 8.7 Hz, 2H), 7.13 (d, J = 8.7 Hz, 2H), 5.16, 5.10 (ABq, JAB= 12.3 Hz, 2H), 5.09 (s, 1H), 4.76 (s, 1H), 4.44 (dd, J= 11.4, 4.8 Hz, 1H), 3.18-3.07 (m, 1H), 2.87-2.57 (m, 5H), 2.20 (d, J = 18.3 Hz, 1H), 2.14-1.98 (m, 2H), 1.91-1.80 (m, 2H),1.80-1.61 (m, 4H), 1.56-1.39 (m, 4H), 1.39-1.25 (m, 6H), 1.34 (s, 3H), 1.22 (s, 3H), 1.19 (s,3H), 1.17-1.0 (m, 4H), 0.97 (s, 3H), 0.91 (s, 3H), 0.88 (s, 3H), 0.85 (s, 6H), 0.79 (m, 1H),0.75 (s, 3H); ESI-MS: mlz 901.46 (M+Na)t

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:
Patent; HETERO RESEARCH FOUNDATION; BANDI, Parthasaradhi Reddy; KURA, Rathnakar Reddy; GAZULA LEVI, David Krupadanam; ADULLA, Panduranga Reddy; KASIREDDY, Bhaskar Reddy; (84 pag.)WO2017/64628; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2589-11-9, name is 6-Chloro-1H-imidazo[4,5-c]pyridine, 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. Safety of 6-Chloro-1H-imidazo[4,5-c]pyridine

C2. Methyl 5-(6-chloro-1H-imidazo[4,5-c]pyridin-1-yl)-3-hydroxythiophene-2-carboxylate (Compound C2a) and Methyl 5-(6-chloro-3H-imidazo[4,5-c]pyridin-3-yl)-3-hydroxythiophene-2-carboxylate (compound C2b) To a mixture of 0.68 g of 6-chloro-1H-imidazo[4,5-c]pyridine and 0.65 g of 2,2,6,6-tetramethylpiperidine in 100 ml chloroform is slowly added a solution of 0.87 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate in 40 ml chloroform. The reaction mixture is stirred for 12 h at room temperature. After washing with water (3 x 50 ml) the organic layer is separated, dried with MgSO4 and concentrated to a volume of about 100 ml. The residue is treated with n-hexane until precipitation takes place. The solid is filtered and the procedure is repeated once again. The combined solids are dried under vacuum to yield the title compounds as an isomeric mixture, which is used for the next step (example B3) without further purification. LC-MS (MH+ found) = 310.0 (isomeric mixture)

The synthetic route of 2589-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 4SC AG; EP2017277; (2009); A1;,
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. 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Chloro-3,5-dimethoxybenzene

1-Chloro-3,5-dimethoxybenzene (70g, 406mmol) and Pyridine Hydrochloride (468g, 4055mmol) are placed in a round bottom flask and refluxed at 200 C for 24 hours. After the reaction is completed, cool to room temperature and slowly pour into distilled water and stirred for 1 hour.The solid was filtered to give 51.6 g (88%) of intermediate (Int-7).

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 7051-16-3.

Reference:
Patent; Samsung SDI Co., Ltd; Samsung Electronics Co., Ltd.; Lee Seung-jae; Kim Chang-u; Kim Byeong-gu; Kim Hyeong-seon; Ryu Dong-wan; Shin Chang-ju; Jang Gi-po; Seo Min-seok; Jeong Seong-hyeon; (39 pag.)KR102044943; (2019); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2729-34-2, 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. 2729-34-2 name is 3,5-Dichloro-4-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.

To a suspension of ethyl 2-cyanoacetimidate hydrochloride (0.50 g, 3.36 mmol, Eq: 1.00) in ethanol (5.2 mL), was added 3,5-dichloro-4-fluoroaniline (606 mg, 3.36 mmol, Eq: 1.00). The suspension was stirred overnight at room temperature, under a nitrogen atmosphere. The reaction mixture was filtered to remove the salts. The clear yellow filtrate was then treated with hydrazine (in water) (313 mg, 310 mu, 3.42 mmol, Eq: 1.02) and heated in an oil bath at 80- 85C for 4.5 h. The reaction was cooled to room temperature and concentrated. The residue was partitioned between EtOAc and water. The organic phase was removed, washed with brine, dried (Na2S04) and concentrated over celite. The crude material was purified by flash chromatography (silica gel, SF 15-24 g, 20% to 100% EtOAc in hexanes) to give a light brown oil, which was further purified by HPLC (reverse phase, Sunfire Prep C18 OBD [5 uM; 30×100 mm], 5% to 95% acetonitrile in water (each containing 0.1% TFA)). The product-containing fractions were combined and freeze-dried. The freeze-dried material was taken up in EtOAc and washed with aqueous NaHC03 (lx) and water (2x). The organic phases was dried (Na2S04) and concentrated. The residue was dissolved in acetonitrile-water and freeze-dried to give 45 mg (5%) of desired product as an off-white solid. MS m/z 261, 263 [M+H]

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/135423; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 821-10-3,Some common heterocyclic compound, 821-10-3, name is 1,4-Dichlorobut-2-yne, molecular formula is C4H4Cl2, 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: K2CO3 (3a, 210 mg, 1.5 mmol) was added to a solution of b-ketoesters 5a-c (0.5 mmol) in acetone (10 mL) at 25 C. The reaction mixture was stirred at 25 C for 10 min. 1,4-Dichloro-2-butyne (2, 68 mg, 0.55 mmol) was added to the reaction mixture at reflux. The reaction mixture was stirred at 56 C for 8 h. The reaction mixture was cooled to 25 C and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with CH2Cl2 (320 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc20/1e10/1) afforded 6a-c.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dichlorobut-2-yne, its application will become more common.

Reference:
Article; Chan, Chieh-Kai; Lu, Yi-Ju; Chang, Meng-Yang; Tetrahedron; vol. 71; 51; (2015); p. 9544 – 9549;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 108-41-8,Some common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, molecular formula is C7H7Cl, 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-methylbenzene, 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