Month: August 2021

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. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3,6-Dichloro-1,2,4,5-tetrazine

General procedure: In a 100 mL round bottom flask, was introduced the diol(0.66 mmol), s-collidine (0.79 mmol) and 20 mL of dry dichloromethane and the mixture was stirred at room temperature. 3,6-dichloro-s-tetrazine 1 (0.66 mmol) was dissolved in dry dichloromethane and added dropwise in the flask. After 2 h the reaction is complete (TLC) and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography on silica gel (eluent from petroleum ether/ethyl acetate 7/3 to pure ethyl acetate). Compound 2a was isolated as pink solid in 58 % yield(0.22 g). M. p.: 131 C.1HNMR (400MHz, Acetone-d6): delta (ppm) 5.49 (t, 2H, 3JHF= 13.19Hz, (CF2)8CH2 – O); 4.18 (t, 2H, 3JH-F = 14.79 Hz,(CF2)8CH2 – OH). 13CNMR (100MHz, Acetone-d6): delta (ppm) 167.1 (CTz-O);166 (CTz-Cl); 100-120 ((CF2)8); 65.3 (t, 2JC-F = 26.83 Hz,(CF2)8CH2 – O); 60.4 (t, 2JC-F = 24.93Hz, (CF2)8CH2 – OH).19F NMR (376 MHz, Acetone-d6): delta (ppm) -119.93 (m,2F); -122.33 (m, 10F); -123.49 (m, 2F); -123.87 (m, 2F).

According to the analysis of related databases, 106131-61-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guermazi, Refka; Royer, Lorna; Galmiche, Laurent; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Journal of Fluorescence; vol. 26; 4; (2016); p. 1349 – 1356;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 56961-77-4

EXAMPLE 10 6-(2,3-Dichlorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 109, structure 4 of Scheme II, where R1 =2,3-dichlorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9). From Compound 9 (68.0 mg, 0.21 mmol) and commercially available 2,3-dichlorobromobenzene (40.1 mg, 0.18 mmol, Lancaster) was obtained a crude product which was isolated and purified by reverse phase HPLC (ODS column, 97% methanol/water, 3.0 mL/min) to afford 20 mg (29%) of Compound 109. Data for Compound109: 1 H NMR (400 MHz, CDCl3)7.39 (dd, J=8, 1.6, 1H), 7.19 (dd, J=16.8, 1H), 7.23 (dd, J=4, 1.6, 1H), 7.11 (d, J=1.6, 1H), 7.05 (dd, J=8, 1.6, 1H), 6.46 (d, J=8, 1H), 5.34 (s, 1H), 3.82 (br s, 1H), 1.99 (s, 3H), 1.32 (s, 6H).

The synthetic route of 56961-77-4 has been constantly updated, and we look forward to future research findings.

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

Electric Literature of 2687-12-9,Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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 cinnamyl chloride (905 ml, 6.5 mol), diisopropylamine (1.37 1, 9.75 mol), potassium carbonate (0.90 kg, 6.5 mol), potassium iodide (54 g, 0.325 mol), toluene (2.1 l) and methanol (0.50 1) is stirred at reflux temperature for 20 hours. The mixture is cooled to 25 C and water (5.2 1) is added. Phases are separated and the organic phase is extracted with brine. Organic phase is concentrated under reduced pressure (50 C) and then water (10.4 1) and toluene (2.6 l) are added and the pH is adjusted to 2 by addition of concentrated hydrochloric acid (-500 ml). The resulting mixture is stirred for 15 minutes and the phases are separated. The aqueous phase is re-extracted twice with toluene (2 x 2.6 l). Then the pH of the aqueous phase is adjusted to 12 by addition of 8 M aqueous sodium hydroxide solution (750 ml). To the resulting white suspension is added heptane (5.2 l) and the mixture is stirred for 15 minutes. Phases are separated and aqueous phase is re-extracted twice with heptane (2 x 2.6 l). Combined organic phases are dried over Na2SO4 and concentrated to give 1.32 kg (93 % yield) of DIPCA.

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

Reference:
Patent; LEK Pharmaceuticals d.d.; EP2364966; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 104-77-8,Some common heterocyclic compound, 104-77-8, name is 3-Chloro-N,N-diethylpropan-1-amine, molecular formula is C7H16ClN, 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 IV Bis[3-(diethylamino)propyl]6-oxo-6H-dibenzo[b,d] pyran-3,8-dicarboxylate dihydrochloride A mixture of 11.0 g (0.04 mole) of 6-oxo-6H-dibenzo [b,d]pyran-3,8-dicarboxylic acid, 18.0 g (0.12 mole) of gamma-diethylaminopropyl chloride and 400 ml of isopropyl alcohol are stirred and heated to its reflux temperature. A catalytic amount of benzyltrimethylammonium chloride. 0.3 ml of a 60% aqueous solution, is added and the reaction mixture heated to reflux for an additional 24 hours. On cooling, the reaction mixture is filtered, and the residue washed with isopropyl alcohol. This product is dissolved in boiling ethanol, treated with charcoal, filtered and cooled to room temperature. After standing for 1 hour, the gelatinous precipitate which appears is filtered and the filtrate cooled to -20C. The product which forms is filtered, washed with ethanol and again recrystallized from ethanol to yield the desired bis[3-(diethylamino)propyl] 6-oxo-6H-dibenzo[b,d]pyran-3,8-dicarboxylate dihydrochloride as a tan-colored solid, soluble in water and having a m.p. of 250-1C. (dec.) (placed in m.p. bath previously heated at 240 C.), lambdamax 294, and E1cm 1% 464.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-N,N-diethylpropan-1-amine, its application will become more common.

Reference:
Patent; Richardson-Merrell Inc.; US3933893; (1976); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13918-92-8, 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 13918-92-8 as follows.

General procedure: To a mixture of 3-amino-2-methyl-thieno[2,3-d]pyrimidin-4(6H)-one (1.0 mmol) (8 and 9) and benzenesulfonyl chloride (1.1 mmol) in DCM (10 mL) was added dropwise pyridine (1.2 mmol) in dichloromethane (2 mL). The resulting mixture was stirred at room temperature for 12 hrs. The mixture was concentrated under reduced pressure, and theresidue was treated with water (30 mL). The aqueous mixture was neutralized by the addition of aqueous 10% HCl solution and extracted with DCM (230 mL). The organicphase was washed with aqueous saturated NH4Cl solution and brine. The organic layer was separated and dried over anhydrous MgSO4, filtered, and concentrated under reducedpressure to give the crude product, which was purified by silica gel chromatography to produce the pure corresponding compounds.

According to the analysis of related databases, 13918-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nie, Li Fei; Bozorov, Khurshed; Huang, Guozheng; Zhao, Jiangyu; Niu, Chao; Aisa, Haji Akber; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 193; 10; (2018); p. 656 – 667;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7006-52-2, name is N-Methyl-3-chloroaniline, molecular formula is C7H8ClN, 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. Safety of N-Methyl-3-chloroaniline

The suitable omega-bromoalkanoyl chloride (0.7 mmol) was added dropwise to a stirred ice-cooled solution of the suitable aniline (0.33 mmol) and NaHCO3 (0.10 g, 1.22 mmol) in EtOAc (0.4 mL) and water (0.4 mL), and the resulting mixture was stirred at room temperature for 20 min. Water was added and the aqueous phase was extracted three times with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford a crude residue that was used for the next step, without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7006-52-2, its application will become more common.

Reference:
Article; Spadoni, Gilberto; Bedini, Annalida; Bartolucci, Silvia; Pala, Daniele; Mor, Marco; Riccioni, Teresa; Borsini, Franco; Cabri, Walter; Celona, Diana; Marzi, Mauro; Tarzia, Giorgio; Rivara, Silvia; Minetti, Patrizia; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 8 – 35;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 139512-70-2, The chemical industry reduces the impact on the environment during synthesis 139512-70-2, name is 4-Chloro-5-fluorobenzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

General procedure: Intermediate compound 5 (0.2 g, 1.24 mmol) and benzil 6d (0.26 g, 1.24 mmol) were weighed and dissolved in 20 mL glacial acetic acid. This mixture was refluxed for 2.5hr. The completion of reaction was monitored by TLC. The reaction mixture was cooled and poured into crushed ice. The precipitated product was filtered off and washed with cold water. The product was then purified by column chromatography using hexane: ethyl acetate as mobile phase. The pure fractions obtained were dried and concentrated to obtain white solids of product 7d. (yield 82%, m.p. 110-112 C).

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, 4-Chloro-5-fluorobenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Patel, Saloni B.; Patel, Bhumika D.; Pannecouque, Christophe; Bhatt, Hardik G.; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 230 – 240;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, 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 19752-55-7, SDS of cas: 19752-55-7

EXAMPLE 2 27 Grams of powdery magnesium (purity 99.5percent) was dispersed in 200 ml of diethyl ether. A solution obtained by dissolving 226 g of 1-bromo-3,5-dichlorobenzene in 800 ml of diethyl ether was added dropwise to the dispersion heated at about 40° C., and after the addition, the mixture was stirred at the same temperature for 2 hours to react them whereby 3,5-dichlorophenylmagnesium bromide was produced.

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

Reference:
Patent; Ishihara Sangyo Kaisha Limited; US4230642; (1980); A;,
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. 38762-41-3, name is 4-Bromo-2-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 38762-41-3

General procedure: Method A: To a solution of 3a (150 mg, 0.47 mmol) in a mixture of dry DME (3 mL) and dry EtOH (3 mL), bis(triphenylphosphine)palladium(II) dichloride (17 mg, 0.02 mmol) was added. After 30 min, a solution of sodium carbonate (299 mg, 2.82 mmol) in H2O(2 mL) and a solution of 5-formyl-2-furanylboronic acid 4 (93 mg,0.66 mmol) in dry EtOH (1.5 mL) were added in this order. The reaction was heated under reflux for 12 h. After this time, H2O (4 mL)was added at 25 C and the organic phase was extracted with EtOAc(3 5 mL), dried over sodium sulfate, filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (2% EtOAc in petroleum ether) to give 5a as orange solid(79 mg, 60%). Method B: To a suspension of 16a (1.0 g, 4.8 mmol) in H2O (20 mL), HCl (37%, 2 mL) was added. The resulting solution was cooled at 0 C and a solution of sodium nitrite (397 mg, 5.76 mmol) in H2O (2 mL) was added dropwise. After 1 h, a solution of 17(400 mL, 4.8 mmol) in acetone (2 mL) and solid copper(II) chloride(128 mg, 0.96 mmol) were added. The mixture kept at 25 C for 12 h. EtOAc was added (3 10 mL) and the organic phase was separated, dried over sodium sulfate, filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (2% EtOAc in petroleum ether) to give 5a as orange solid (1.23 g, 90%).

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Vallone, Alessandra; D’Alessandro, Sarah; Brogi, Simone; Brindisi, Margherita; Chemi, Giulia; Alfano, Gloria; Lamponi, Stefania; Lee, Soon Goo; Jez, Joseph M.; Koolen, Karin J.M.; Dechering, Koen J.; Saponara, Simona; Fusi, Fabio; Gorelli, Beatrice; Taramelli, Donatella; Parapini, Silvia; Caldelari, Reto; Campiani, Giuseppe; Gemma, Sandra; Butini, Stefania; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 698 – 718;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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

(First step) Preparation of 2-(3-chloro-5-fluorophenyl)-5-pentylpyrimidine A solution of 3-chloro-5-fluorophenylmagnesium bromide [prepared from 22.7 g (108.3 mmol) of 3-chloro-5-fluoro-bromobenzene and 2.7 g (111.0 mmol) of magnesium, and 100 ml of diethyl ether] in diethyl ether was added by drops to a mixture of 10 g (54.1 mmol) of 2-chloro-5-pentylpyrimidine, 0.4 g (0.5 mmol) of dichloro[1,1′-bis(diphenylphosphino) ferrrocene]palladium, and 300 ml of diethyl ether while being maintained at a temperature lower than -60 C., stirred at the same temperature for 1 hour, and then stirred at 10 C. for 10 hours. A diluted hydrochloric acid in an amount of 300 ml was added to the reaction mixture and extracted with 250 ml of heptane. The organic layer thus obtained was washed with a diluted aqueous sodium bicarbonate solution thrice and water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure and the residue was subjected to silica gel column chromatography (eluent: heptane/toluene=1/1) to obtain 11.0 g of a crude 2-(3-chloro-5-fluorophenyl)-5-pentylpyrimidine. (Yield: 72.8%) This product was used for the subsequent reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33863-76-2, its application will become more common.

Reference:
Patent; Chisso Corporation; US6329027; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics