Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 13065-93-5, name is N1-(4-Chlorophenyl)benzene-1,4-diamine, 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 13065-93-5, category: chlorides-buliding-blocks

[0201] Step 3. To a solution of Compound 8-D (0.4 g, 1.8 mmol) and Compound 8-E(0.31 g, 1.8 mmol) in isopropanol (8 mL) was added p-toluenesulfonic acid (0.36 g, 1.9 mmol). The mixture was sealed and heated in microwave at 120 C for 1 hour. Monitoring by thin layer chromatography (petrol ether: ethyl acetate= 1:1 and Rf at 0.6) showed that Compound 8-E was consumed. The mixture was diluted with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (15 mL x 3). The organic layers were concentrated and the residue was purified by preparative HPLC to give the title compound (38 mg, 1.3%, combined with other 5 batches; purity 79% by HPLC) as a white solid. ?H NMR (400 MHz, DMSO) oe 6.94-6.96 (d, J= 8.4 Hz, 1H), 7.07-7.05 (d, J= 8.4 Hz, 1H), 7.17-7.19 (d, J = 8.8 Hz, 1H), 7.50-7.52 (d, J= 8.4 Hz, 1H), 8.14 (s, 1H), 8.80 (s, 1H), 10.19 (s, 1H). MS:302.9 (M+lj.

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, N1-(4-Chlorophenyl)benzene-1,4-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROPORE THERAPIES, INC.; WRASIDLO, Wolfgang; STOCKING, Emily, M.; WO2014/26039; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 204930-37-0, 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. 204930-37-0 name is 5-Bromo-1,3-dichloro-2-methylbenzene, 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 solution of 5-bromo-1,3-dichloro-2-methylbenzene (1.4 g, 5.8 mmol) in carbon tetrachloride (20 mL) was added N-bromosuccinimide (2.6 g, 14.6 mmol) followed by benzoyl peroxide (71 mg, 0.3 mmol). The reaction was heated at reflux overnight, then cooled to room temperature and filtered through Celite. The solvent was removed in vacuo and the residue was purified via chromatography (100percent hexanes). This provided the product, 5-bromo-2-(bromomethyl)-1,3-dichlorobenzene. 1H NMR (400 MHz, CDCl3) delta 7.50 (s, 2H), 4.68 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,3-dichloro-2-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2162-98-3, 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. 2162-98-3, name is 1,10-Dichlorodecane belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2,3-dihydro-1H-cyclopenta[b]quinolin-9-ylamine (0.45 g, 2.44 mmol), 1,10-dichlorodecane (0.25 g, 1.2mmol), and sulfolane (2 mL) was heated at 190-200 C for 90 h. The resulting mass was stirred with methanol and filtered. The filtrate was concentrated and chromatographedon an Al2O3 column using a gradient from 1 to 25% ofmethanol in methylene chloride. Fractions containing required product were pooled together and evaporated, andthe resulting off-white solid (31 mg, 4.5%) was further purified by crystallization from a methanol/acetone mixture [Mp 250-258 C (dec). 1H NMR (500 MHz, CDCl3) delta1.27-1.43 (m, 12 H), 1.67-1.76 (m, 4 H), 2.20-2.26 (m, 4H), 2.95 (t, 4 H, J = 7.5 Hz), 3.38 (t, 4 H, J = 7.5 Hz), 3.63(t, 4 H, J = 7.0 Hz), 4.46 (t, 4 H, J = 6.5 Hz),7.72 (t, 2 H, J = 7.0 Hz), 7.98 (t, 2 H, J = 7.5 Hz),8.15 (d, 2 H, J = 9.0 Hz), 8.54 (d with fine splitting, 2 H,J = 8.5 Hz), 8.92 (br s, 4 H, NH2).

The synthetic route of 1,10-Dichlorodecane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sharma, Arun K.; Krzeminski, Jacek; Weissig, Volkmar; Hegarty, John P.; Stewart, David B.; Journal of Antibiotics; vol. 71; 8; (2018); p. 713 – 721;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 81067-38-1, A common heterocyclic compound, 81067-38-1, name is 1-Bromo-2,3,5-trichlorobenzene, molecular formula is C6H2BrCl3, 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.

2. 2,3,5-Trichlorobenzeneboronic Acid A solution of 2,3,5-trichlorobromobenzene (8.60 g, 0.033 mole) in dry ether (33 ml) and bromoethane (4.73 ml, 7.31 g, 0.067 mole) was added dropwise to a suspension of magnesium turnings (2.809, 0.12 mole) in dry ether (21.50 ml) at room temperature. The mixture was refluxed for 0.50 hr and cooled to room temperature. The mixture was then added dropwise under nitrogen to a solution of trimethylborate (5.16 ml, 5.16 g, 0.05 mole) in dry ether (8.60 ml) maintaining the temperature below -60 C. This was warmed to room temperature overnight, then cooled in an ice-bath and treated with 2M hydrochloric acid (10 ml). The ether layer was separated, washed with water (2*20 ml), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated in vacuo. The residue was triturated with 40-60 C. petroleum ether, filtered and dried in vacuo. Yield 4.57 g (61%), M.p. 257-260 C.

The synthetic route of 81067-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Wellcome, Inc.; US6255307; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 450-96-4, name is 1-Chloro-2-(trifluoromethoxy)benzene, 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 450-96-4, Computed Properties of C7H4ClF3O

Step 1 : Synthesis of INT-41 INT-41 To a solution of 1 -chloro-2-(trifluoromethoxy)benzene (2.5 mmol) in THF (10 mL) is added 2.5 M n-buthyllithium in hexanes (1 .4 mmol) at -78 C. After 40 min, a solution of DMF (2.8 mmol) in THF (2.5 mL) is added and the mixture is stirred to room overnight. The reaction is quenched with water at 0 C, extracted with EtOAc (3 x 50 mL), the combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography provides 2-chloro-3- (trifluoromethoxy)benzaldehyde (INT-41 ).

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, 1-Chloro-2-(trifluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RGENIX, INC.; MARTINEZ, Eduardo, J.; KAISER, Bernd; TAVAZOIE, Sohail, F.; KURTH, Isabel; GONSALVES, Foster, Casimir; DARST, David, M., Jr.; TAVAZOIE, Masoud, Fakhr; WO2015/106164; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 16429-44-0, A common heterocyclic compound, 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, molecular formula is C6H6BrClN2, 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.

5-Bromo-3-chloro-1 ,2-diaminobenzene (4.6 g; 20 mmol; 1 eq.) is dissolved in EtOH (200 mL) and 2,3-dixydroxy-1 ,4-dioxane (2.5 g, 20 mmol; 1 eq.) is added. The mixture is stirred for 4 h at room temperature and a second portion of 2,3-dihydroxy-1 ,4-dioxane (1.3 g; 10 mmol; 0.5 eq.) is added. After stirring for 24 h at room temperature, the reaction mixture is concentrated and the residue is purified by FCC (EtOAc gradient in hexane) to provide 7- bromo-5-chloroquinoxaline as a beige solid (4.7 g; yield: 92%; UPLC purity: 98%).

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; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Malgorzata; GUZIK, Pawel Szczepan; BIA?AS, Arkadiusz Kacper; PAWLIK, Henryk Edward; BOUTARD, Nicolas Felix Pierre; (439 pag.)WO2016/180537; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1298031-94-3,Some common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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 8-bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (1.2 g, 4.9 mmol), cyclopropylboronic acid (843 mg, 9.8 mmol), Pd(dppf)Cl2 (359 mg, 0.49 mmol) and Na2C03 (1.56 g, 14.7 mmol) in 1,4-dioxane (12 mL) and water (3 mL) was stirred at 90 C under N2 for 48 h. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-35% EtOAc in petroleum ether to yield 6-chloro-8-cyclopropyl-2- methylimidazo[l,2-b]pyridazine (405 mg, 40%). MS m/z 208.0, 210.0 [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 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); 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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H7ClFN

3-Chloro-5-fluorobenzylamine (97 mg, 0.61 mmol) and Et3N (0.24 ml, 1.8 mmol) followed by T3P (0.6 ml, 1.8 mmol) are added at 0 C. to a solution of 3-azido-2-oxo-1-phenylpyrrolidine-3-carboxylic acid (150 mg, 0.61 mmol) in 5 ml of dichloromethane. The reaction mixture is stirred at room temperature under nitrogen for 4 hours. When the reaction is complete, water is added, and the mixture is extracted to exhaustion with dichloromethane. The combined organic phases are subsequently washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration and evaporation, the residue is purified by chromatography on silica gel, giving the product as colourless solid (150 mg, 63% yield); Thin-layer chromatogram: chloroform/methanol=9.5:0.5), Rf: 0.3 LC/MS: 388.1 (M+H at 1. 388 min); HPLC: Rt 5.12 min (HPLC purity 95.15%, 95.46%); 1H NMR (DMSO-d6, 400 MHz): delta [ppm] 9.13 (t, J=6.08 Hz, 1H), 7.70-7.68 (m, 2H), 7.43 (t, J=8.64 Hz, 2H), 7.32-7.29 (m, 1H), 7.24-7.20 (m, 2H), 7.09 (d, J=9.80 Hz, 1H), 4.42-4.34 (m, 2H), 3.95-3.89 (m, 2H), 2.61-2.58 (m, 1H), 2.28-2.22 (m, 1H).

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 90390-33-3.

Reference:
Patent; Merck Patent GmbH; Heinrich, Timo; Zenke, Frank; Calderini, Michel; Musil, Djordje; US2013/296274; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1009102-44-6, These common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, 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.

In step 1 Manufactured 1-(4-chlorophenyl)cyclopropan-1-amine hydrochloride (0.500 g, 2.450 mmol), ethyl 2-chloropyrimidine-5-carboxylate (0.503 g, 2.695 mmol) and N,N-diisopropylethylamine (1.280 mL, 7.350 mmol) was dissolved in 1,4-dioxane (10 mL) at room temperature and stirred at 110 C for 18 hours, and then the temperature was lowered to room temperature to complete the reaction. After the solvent was removed from the reaction mixture under reduced pressure, the concentrate was crystallized from ethanol (5 mL) at room temperature, filtered and washed with ethanol and dried to give the title compound (0.520 g, 66.8%) as a white solid.

The synthetic route of 1009102-44-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 69411-05-8, These common heterocyclic compound, 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, 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.

Example 13 1-(5-Chloro-3-trifluormethyl-anilino)-4-(4-pyridyl-methyl)-phthalazine A suspension of 27.9 g (109 mMol) of 1-chloro-4-(4-pyridyl-methyl)-phthalazine (Example 67A.1 in WO 98/35958) and 21.4 g (109 mMol) of 5-amino-3-chloro-benzotrifluoride (Example 5b) in 500 ml of ethanol and 27.4 ml of 4 N HCl/dioxane is stirred during 3 h a 80 C. After cooling down, the reaction mixture is diluted with 0.3 l of ether, filtrated, and washed with ether. The remaining solid is then taken up in water and EtOAc, brought to alkaline pH by means of NH3 solution, stirred for 15 min at room temperature and then filtered and washed with ether (?raw product). The water layer is removed from the filtrate and extracted twice with ethyl acetate. The organic layers are washed with water and brine, dried over Na2SO4 and evaporated. The residue is combined with the raw product mentioned above, and the solid is dissolved in ethyl acetate and methanol. About 100 g SiO2 are added, followed by evaporation, and the powder is applied onto a silica gel column and eluted with ethyl acetate and subsequently with a mixture of ethyl acetate and methanol (98:2?95:5, v/v). Solving the obtained fractions in ethyl acetate/methanol, partial evaporation and crystallization by addition of ether/hexane leads to the title compound: m.p. 231-232 C.; An. calc. (C21H14N4ClF3) C, 60.81%; H, 3.40%; N, 13.51%; Cl, 8.55%; F, 13.74%; An meas. C, 60.8%; H, 3.4%; N, 13.5%; Cl, 8.5%; F, 13.8%; 1H-NMR (DMSO-d6) 9.63 (s, HN), 8.60 (d, 1H), 8.56 (s, 1H), 8.44 (d, 2H), 8.39 (s, 1H), 8.16 (d, 1H), 8.03 (t, 1H), 7.97 (t, 1H), 7.43 (s, 1H), 7.32 (d, 2H), 4.63 (s, 2H); FAB-MS (M+H)+=415.

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bold, Guido; Dawson King, Janet; Frei, Jorg; Heng, Richard; Manley, Paul William; Wietfeld, Bernhard; Wood, Jeanette Marjorie; US2003/13718; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics