Category: chlorides-buliding-blocks

Reference of 67279-24-7, 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. 67279-24-7 name is 1,4-Dichloro-5,6,7,8-tetrahydrophthalazine, 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 1,4-dichloro-5,6,7,8-tetrahydro-phthalazine (compound 25, 100 mg, 0.492 mmol) in NMP (3 mL) is added 1-[5-trifluoromethyl)-pyrid-2-yl)-piperazine (114 mg, 0.492 mmol) followed by triethyl amine (218 muL, 1.57 mmol). The mixture was heated in a microwave reactor for 140 C. for 60 min. Water was added to the reaction mixture and extracted with EtOAc. The combined arganic extracts were washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (EtOAc/heptane 10% to 70%) to yield 96 mg (49%) of the title compound.1H NMR (400 MHz, CD2Cl2) delta=8.41 (s, 1H), 7.73 (dd, J=9.0 Hz, 2.5 Hz, 1H), 6.79 (d, J=9.0 Hz, 1H), 3.85 (m, 4H), 3.40 (m, 4H), 2.76-2.68 (m, 4H), 1.93 (m, 2H), 1.80 (m, 2H).HR MS (m/z, MH+) meas. 398.1359.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Dichloro-5,6,7,8-tetrahydrophthalazine, and friends who are interested can also refer to it.

Reference:
Patent; Novartis AG; US2010/41663; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 118-69-4, name is 2,6-Dichlorotoluene, 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 118-69-4, Computed Properties of C7H6Cl2

EXAMPLE 1-1 Preparation of 2,4-dichloro-3-methylbromobenzene To a solution of 48.8 g (0.3 mol) of 2,6-dichlorotoluene in 60 ml of carbon tetrachloride, 0.7 g of iron powder and 0.1 g of iodine were added. Then, 52.8 g (0.33 mol) of bromine was dropwise added thereto at room temperature while maintaining the reaction temperature at a level of from 22 to 25 C. After completion of the dropwise addition, the reaction was continued at the same temperature until generation of hydrogen bromide ceased. After the reaction, the reaction solution was added to 300 ml of ice water and extracted with 300 ml of 1,2-dichloroethane. The organic layer was separated and washed sequentially with water, a saturated sodium hydrogen sulfite aqueous solution, water and a saturated sodium chloride aqueous solution. Then, the solvent was distilled off under reduced pressure to obtain 71.9 g (yield: 99.5%) of desired 2,4-dichloro-3-methylbromobenzene. Melting point: 32-33 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorotoluene, and friends who are interested can also refer to it.

Reference:
Patent; Nissan Chemical Industries Ltd.; US4942246; (1990); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1435-48-9, A common heterocyclic compound, 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, molecular formula is C6H3Cl2F, 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.

Reference Example 2-44 2,4-Dichloro-5-fluorobenzoic acid Following the procedure described in Reference Example 2-25, the title compound was prepared from 2,4-dichloro-1-fluorobenzene (66% yield). NMR (CDCl3) delta: 7.59 (1H, d, J=6.2 Hz), 7.85 (1H, d, J=8.8 Hz), 8.28 (1H, br s).

The synthetic route of 1435-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Uchikawa, Osamu; Mitsui, Keita; Asakawa, Akiko; Morimoto, Shigeru; Yamamoto, Masataka; Kimura, Hiroyuki; Moriya, Takeo; Mizuno, Masahiro; US2003/187014; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 93-50-5, 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. 93-50-5, name is 4-Chloro-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6,8-dichloro-4-oxo-chromene-2-carboxylic acid (Int-2, 1.3 g, 5.02 mmol) in DCM (20 mL) was added 4-chloro-2-methoxyaniline (949 mg, 6.02 mmol), DIPEA (1.15 g, 8.9 mmol) and HATU (3.3 g, 8.9 mmol) at room temperature and the resulting mixture was then stirred at room temperature for 18 hours. After the reaction was completed, the mixture was diluted with water (30 mL) and extracted with EtOAc (50 mL) three times. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by silica gel flash chromatography (elution with PE/EtOAc=lO: 1-1:4) to give 6,8-dichloro-N-(4-chloro-2-methoxyphenyl)-4-oxo-chromene-2-carboxamide (1.6 g, 80 %) as a yellow solid. MS obsd. (ESP) [(M+H)+]: 398.1.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-2-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; LIANG, Chungen; LIU, Yongfu; TAN, Xuefei; WU, Jun; WANG, Jianping; (134 pag.)WO2020/79106; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 6276-54-6, 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 6276-54-6 as follows.

[0086] Under stirring, a solution of di-tert-butyl di-carbonate (23.79 g, 110 mmol) in chloroform (50 mL) is slowly addedinto a solution of 3-chloropropylamine hydrochloride (11.0 g, 110 mmol) and triethylamine (18.42 mL, 130 mmol) inchloroform (50 mL). After stirring overnight at room temperature, a brown oil is obtained as a crude product. Thencompound (8-2) (22 g, 95%) as a colorless solid is produced by Kugelrohr distillation at a temperatures of less than 48 C.

According to the analysis of related databases, 6276-54-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangzhou Bensheng Pharmaceutical Co., Ltd.; XU, Rongzhen; XIE, Fuwen; LAI, Hongxi; RONG, Frank; EP2615092; (2013); 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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Chloro-3-methoxyaniline

A stirred solution of 4-chi oro-3-methoxy-aniline (92, 5 g, 31.73 mmol) and diethyl 2- (ethoxymethylene)propanedioate (77, 10.29 g, 47.59 mmol, 9.53 mL) was heated to 100C and stirred for 2 hours and then further heated to 165 C and stirred for an additional hour. Diphenyl ether (50.0 mL) was added to the resulting solution and the reaction was heated to 280 C and stirred for 5 hours. The resulting reaction mixture was cooled to room temperature, pet ether (250 mL) was added and the reaction was stirred for 10 minutes at room temperature. The resulting solid was filtered, washed with pet ether and dried under vacuum to yield ethyl 6-chloro-4- hydroxy-7-methoxy-quinoline-3-carboxylate (93, 8.0 g, 28.40 mmol, 89.51% yield) as an off white solid. LCMS (ES+): m/z 282 [M + H]+

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 13726-14-2.

Reference:
Patent; C4 THERAPEUTICS, INC.; NASVESCHUK, Christopher, G.; HENDERSON, James, A.; VORA, Harit, U.; VEITS, Gesine, Kerstin; PHILIPS, Andrew, J.; (576 pag.)WO2020/51235; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, molecular formula is C9H11Cl, 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. category: chlorides-buliding-blocks

General procedure: To a solution of 4-phenylbutyl benzoate 1a (127 mg, 0.5 mmol) and N-hydroxyphthalimide (8.16 mg, 0.05 mmol) in CH3CN (1.7 mL) was added cerium(IV) ammonium nitrate (548 mg, 1.0 mmol) at 0 C. The reaction mixture was immediately warmed to room temperature and stirred for 2 h. The mixture was then filtered through a short column of alumina (hexane-EtOAc 1:1), and the filtrate was concentrated. The residue was purified with flash column chromatography (silica gel, hexane-EtOAc 70:1 to 50:1) to provide 4-benzoyloxy-1-phenylbutyl nitrate 2a in 81% yield (128 mg). 1.0 mmol) at 0 C. The reaction mixture was immediately warmed to room temperature and stirred for 2 h. The mixture was then filtered through a short column of alumina (hexane-EtOAc 1:1), and the filtrate was concentrated. The residue was purified with flash column chromatography (silica gel, hexane-EtOAc 70:1 to 50:1) to provide 4-benzoyloxy-1-phenylbutyl nitrate 2a in 81% yield (128 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104-52-9, its application will become more common.

Reference:
Article; Kamijo, Shin; Amaoka, Yuuki; Inoue, Masayuki; Tetrahedron Letters; vol. 52; 36; (2011); p. 4654 – 4657;,
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. 694-80-4, name is 1-Bromo-2-chlorobenzene, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-2-chlorobenzene

Sub 1-I-I-32 (109.66 g, 543.8 mmol) obtained in the above-Was placed in a round bottom flask,1-bromo-2-chlorobenzene (156.17 g, 815.7 mmol)And K2CO3 (225.48 g, 1,631.4 mmol)And copper (3.46 g, 54.4 mmol),Then, dibenzo 18-crown-6 (9.80 g, 27.2 mmol) was added thereto,nitrobenzene (2,700 mL) to 220 DEG C, and the reaction mixture is stirred for 24 hours.When the reaction is terminated, the reaction is filtered through silicagel filterAfter the reaction mixture was quenched with water, the water in the reaction mixture was removed,After filtration under reduced pressure,Dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 127.33 g (yield: 75%) of the 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:
Patent; Duksan Neolux Co.,Ltd.; Yoon Jin-ho; Jeong Ho-yeong; Park Mu-jin; Kim Jeong-seok; Lee Seon-hui; (46 pag.)KR2018/128292; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 5719-08-4, These common heterocyclic compound, 5719-08-4, name is 4-Chloro-9H-pyrimido[4,5-b]indole, 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: To a 100 mL round bottom flask were added appropriate 4-chloro-pyrimido[4,5-b]indole 11 or 12 (1 equivalent), 4-methoxy-N-methylaniline (4 equivalents), conc. HCl (2 drops), and BuOH (25 mL). The reaction mixture was heated to reflux for 72 h. After cooling to rt, silica gel (500 mg) was added, and BuOH was removed under reduced pressure to afford a silica gel plug. The plug was transferred on top of a column packed with silica gel, 20 times the weight of plug, and was eluted with 0.5% and 1% MeOH in CHCl3. Fractions containing the product (TLC) were pooled, and the solvent was evaporated to afford target compounds 2 or 3.

Statistics shows that 4-Chloro-9H-pyrimido[4,5-b]indole is playing an increasingly important role. we look forward to future research findings about 5719-08-4.

Reference:
Article; Devambatla, Ravi Kumar Vyas; Li, Wei; Zaware, Nilesh; Choudhary, Shruti; Hamel, Ernest; Mooberry, Susan L.; Gangjee, Aleem; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3423 – 3430;,
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. 328-84-7, name is 3,4-Dichlorobenzotrifluoride, A new synthetic method of this compound is introduced below., Recommanded Product: 3,4-Dichlorobenzotrifluoride

PRODUCTION EXAMPLE 4 Production of an Intermediate Aniline Compound 3.00 Grams of 2,5-difluoro-4-mercaptoaniline hydrochloride, 6.60 g of 3,4-dichlorobenzotrifluoride and 4.90 g of potassium carbonate were dissolved in 30 ml of dimethylformamide, and the resulting solution was stirred for 6 hours at a temperature of from 100 to 110 C. in an oil bath. Thereafter, the reaction solution was poured into water and extracted with three 100-ml portions of diethyl ether. The extract obtained was washed with water, dried, filtered and concentrated. The residue obtained was subjected to chromatography on silica gel to obtain 3.60 g of 2,5-difluoro-4-[2-chloro-4-(trifluoromethyl)phenylthio]aniline. Yield 69% m.p. 95.9 C. 1 H-NMR (CDCl3):

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; Sumitomo Chemical Company, Limited; US5116875; (1992); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics