Author: Jessica.F

These common heterocyclic compound, 126764-17-8, name is 1-Chloro-6,6-dimethylhept-2-en-4-yne, 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. Computed Properties of C9H13Cl

Example-6: Preparation of crystalline Form-I of Terbinafine compound of formula-3 Added 60 grams of sodium carbonate to a solution of 75 grams of N-methyl naphthylmethyl amine hydrochloride in 450 ml of water and at an ambient temperature. Stirred the reaction mixture for 45 minutes at an ambient temperature. Cooled the reaction mixture to 10-150C. Added 112.5 grams of 6,6-dimethyl-l-chlorohept-2-ene-4-yne to the above reaction mixture at 10-15C. Heated the reaction mixture to 70-750C. Stirred the reaction mixture for 6 hours at 70-750C. Cooled the reaction mixture to 25-35C. Quenched the reaction mixture with water. Extracted the reaction mixture thrice with methylene chloride. Combined all the organic phases and washed thrice with water. Separated the organic phase. Distilled the organic phase completely under reduced pressure at below 500C. Added 50 ml of isopropyl alcohol to the above reaction mixture. Distilled the solvent completely under reduced pressure at below 500C. Cooled the reaction mixture to 25-350C. Added 180 ml of isopropyl alcohol to the above reaction mixture and heated to reflux. Stirred the reaction mixture at reflux for 20 minutes. Cooled the reaction mixture to 0-50C. Stirred the reaction mixture for 60 minutes at 0-50C. Filtered the precipitated solid and washed with chilled isopropyl alcohol. Dried the material to get the crystalline Form-I of Terbinafme. Yield: 74 grams

The synthetic route of 1-Chloro-6,6-dimethylhept-2-en-4-yne has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SATYANARAYANA REDDY, Manne; RAMA SUBBA REDDY, Karamala; WO2007/96904; (2007); A2;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 33050-38-3, name is 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, 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 33050-38-3, Application In Synthesis of 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine

General procedure: Appropriate 6-chloro-[1 ,2,4]triazolo[4,3-b]pyridazine (1 eq) or 6-chloro- [1 ,2,4]triazolo[3,4-a]phtalazine (1 eq), potassium carbonate (3 to 4 eq) and the appropriate phenol, thiophenol (1 to 4 eq, 1 eq is preferentially used when R1 = CI) were dissolved in ?,?-dimethylformamide under nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature or at 100-1 10C, or 5-30 minutes at 100-170C on microwave irradiation. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2S04, filtered and evaporated to dryness. The residue was purified by chromatography on silica gel, precipitated, triturated in the appropriate solvent, or used without further purification to obtain the desired 6-aryl-[1 ,2,4]triazolo[4,3-b]pyridazine, or 6-aryl-[1 ,2,4]triazolo[3,4-a]phtalazine.This protocol was used to prepare the following compounds: Cpd.1 -1 , Cpd.1 -3, Cpd.1 -4, Cpd.1 -7, Cpd.1 -8, Cpd.1 -9, Cpd.1 -10, Cpd.1 -1 1 , Cpd.1 -12, Cpd.1 -13, Cpd.1 -14, Cpd.2-1 , Cpd.2-3, Cpd.2-4 and other compounds of the invention that contain a biphenyloxy, a pyridinylphenyloxy, a thiazolylphenyloxy, or a thiopenylphenyloxy group in the 6-substituted position of the [1 ,2,4]triazolo[4,3-b]pyridazines or 6-substituted position of the [1 ,2,4]triazolo[3,4-a]phthalazine (but further information about conditions and purification are reported in Tables of Example 2).

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, 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENFIT; BOUROTTE, Maryline; DELHOMEL, Jean-Francois; DUBERNET, Mathieu; GOUY, Marie-Helene; WO2013/45519; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1020198-58-6, These common heterocyclic compound, 1020198-58-6, name is 2-Bromo-1-chloro-3,5-difluorobenzene, 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 93 Preparation of Compound 93 (lR,4S,12aR)-N<2-chloro-4,6-dtf octahydro-l,4-methanodipyrido[l,2-a:r,2'-d]pyrazme-9-carboxarnide Step 1 A 5 mL microwave vial was charged with 2-bromo-l-chioro-3,5- difluorobenzene (540 mg, 2.4 mmol), cuprous cyanide (436 mg, 4,87 mmol), tetrakis(triphenylphosphme)palladium (63 mg, 0.05 mmol), sealed, and evacuated/backfilled with nitrogen. To this was added 5 mL degassed DMF. The sealed vessel was heated at 110 C for 18 hours, diluted with ethyl acetate, and washed sequentially with twice 9:1 NH40H:NH4Ci aq twice 5% LiCl(aq ), and brine. The organic phase was then dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by flash chromatography (100% hexanes) to afford 2-chloro-4,6- difiuorobenzonitrile. - MR (400 MHz, Chloroform-*/) delta 7.13 (dt, J ------- 8.0, 1.9 Hz, 1H), 6.93 (td, J = 8.5, 2.3 Hz, 1H). The synthetic route of 1020198-58-6 has been constantly updated, and we look forward to future research findings. Reference:
Patent; GILEAD SCIENCES, INC.; JIN, Haolun; LAZERWITH, Scott, E.; MARTIN, Teresa, Alejandra, Trejo; BACON, Elizabeth, M.; COTTELL, Jeromy, J.; CAI, Zhenhong, R.; PYUN, Hyung-Jung; MORGANELLI, Philip, Anthony; JI, Mingzhe; TAYLOR, James, G.; CHEN, Xiaowu; MISH, Michael, R.; DESAI, Manoj, C.; WO2014/100323; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 108-70-3, name is 1,3,5-Trichlorobenzene, 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 108-70-3, Application In Synthesis of 1,3,5-Trichlorobenzene

General procedure: Aryl chloride (1.0 mmol),arylboronic acid (1.2 mmol), precatalyst (0.05 mmol), preligand (0.05 mmol),and base (3.0 mmol) were added to a Schlenk tube equipped with a magnetic stirring bar, a septum, and a reflux condenser. After the tube was evacuated and refilled with nitrogen gas three times, degassed solvent (3 mL) was added via a syringe. The reaction mixture was heated to the described temperature for the required time. After the reaction cooled to room temperature, water (10 mL) was added tothe reaction mixture. The resulting mixture was extracted with CH2Cl2(3 x 10 mL). The combined organic layers were dried over anhydrous Na2SO4,filtered and concentrated to dryness. The remaining residue was analyzed by GC(Table 1) or purified by flash chromatogram phy on silica gel with ethylacetate-hexanes (0-20% ethyl acetate in hexanes) of as eluents.

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

Reference:
Article; Hu, Feng; Kumpati, Blessy N.; Lei, Xiangyang; Tetrahedron Letters; vol. 55; 52; (2014); p. 7215 – 7218;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 33786-89-9, These common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, 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.

(1) To a solution of 5-chloro-1,3-phenylenediamine (2.00 g) in acetic acid (20 mL) was added 2,5-dimethoxytetrahydrofuran (1.8 mL). After 4 hours at reflux, the reaction mixture was concentrated. The residue was suspended in satd. NaHCO3 and EtOAc. The reaction mixture was filtered and the organic layer was collected, washed with satd. NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by chromatography (silica gel: EtOAc/hexane: 1/4) afforded 0.54 g of 3-chloro-5-(1-pyrrolyl)aniline. MS (m/z) 193 (MH+).

Statistics shows that 5-Chloro-m-phenylenediamine is playing an increasingly important role. we look forward to future research findings about 33786-89-9.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1307455; (2005); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature 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: To a solution of diyne (50 mg) in dry solvent (5mL) in microwave reaction vessel propargyl halide 7b/c/e/f (2 equiv.) and Mo(CO)6 (5 mol%) were added andthe reaction mixture was irradiated in a CEM Discover microwave synthesizer for10 min. under standard conditions. Afterthe completion of reaction (TLC monitoring), the solvent was concentrated atreduced pressure and the crude product was purified by silica gel columnchromatography

The synthetic route of 821-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kotha, Sambasivarao; Sreevani, Gaddamedi; Tetrahedron Letters; vol. 56; 43; (2015); p. 5903 – 5908;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 94-97-3, 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. 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 5-(2-nitrophenyl)-1H-benzo[d][1,2,3]triazole 6.8 g (yield: 68%) of 5-(2-nitrophenyl)-1H-benzo[d][1,2,3]triazole was obtained by performing the same procedure as in of Preparation Example 1, except that 6.5 g of 5-chloro-1H-benzo[d][1,2,3]triazole was used instead of 5-bromo-1H-benzo[d]imidazole used in of Preparation Example 1.

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-1H-benzo[d][1,2,3]triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DOOSAN CORPORATION; Bae, Hyung Chan; Beak, Young Mi; Kim, Tae Hyung; Park, Ho Cheol; Lee, Chang Jun; Shin, Jin Young; US2015/171344; (2015); A1;,
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. 367-22-6, name is 4-Chloro-3-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H5ClFN

A solution of methyl 4-nitro-3-(1-piperidinylmethyl)benzoate (16.05 g, 57.7 mmol) in Tetrahydrofuran (THF) (100 mL) and methanol (100 mL) was treated with LiCH (250 mL, 250 mmol) and stirred at ambient temperature for 4 hours. The mixture was concentrated togive crude 4-nitro- 3-(1-piperidinylmethyl)benzoic acid (20.51 g). The acid intermediate was suspended in SOd2 (50 mL, 685 mmol), refluxed for 1 .5 hours, and concentrated to give 4- nitro-3-(1-piperidinylmethyl)benzoyl chloride (LCMS in meoh, ES+279, methyl ester). The acyl chloride was suspended in dichloromethane (DCM) (100 mL), treated with 4-chloro-3- fluoroaniline (7.97 g, 54.8 mmol), Et3N (12.06 mL, 87 mmol), and stirred at ambienttemperature overnight. Additional Et3N (4 mL), DCM (11 mL), and aniline (418 mg) was added, and the reaction was stirred overnight. The suspension was quenched with sat. NaHCO3, extracted with DCM 2x, washed with sat. NaHCO3 lx, Brine, dried with Na2SO4, filtered, and concentrated. Purification by silica gel column chromatography (0-50% EtOAc/Hexane) gave N-(4-chloro-3-fluorophenyl)-4-nitro-3-(1-piperidinylmethyl)benzamide (13.86 g, 35.4 mmol, 61.3 % yield) as yellow solid. LC/MS (m/z) ES+ = 279.3 (M+1)+

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; JEFFREY, Jerry; TANG, Jun; TAI, Vincent Wing-Fai; TEMELKOFF, David; VELTHUISEN, Emile Johann; WEATHERHEAD, Jason Gordon; (101 pag.)WO2018/2902; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 344-19-4, 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. 344-19-4, name is 2,6-Dichloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Cu-powder (5.3 g) was added with stirring to 2,6-dichloro-4-fluoro-aniline (100 g, 0.56 mol) dissolved in diethyldisulfide (400 mL) and the mixture was heated at 80 C. Tert-butyl nitrite (86g, 1 .5 equiv.) was added slowly over a period of 1 hour (exothermic reaction) and stirring was continued for an additional hour at 80 C.Work-up: Excess diethyl disulfide was evaporated in vacuo and the residual crude was treated with diluted aqueous hydrochloric acid. The aqueous phase was extracted with toluene. Thr organic phase was washed sequentially with hydrochloric acid and water, dried over mag35 nesium sulfate. Evaporation of the solvent gave 1 ,3-dichloro-2-ethylsulfanyl-5-fluoro-benzene asa brownish oil (111 g, 0.50 mol, 89%) which was used without further purification in the next step.1H NMR (CDCI3, 400 MHz): D = 7.2 (d, 2 H), 2.9 (q, 2 H), 1.2 (t, 3H).

The synthetic route of 2,6-Dichloro-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; KRAUS, Helmut; CALO, Frederick; WITSCHEL, Matthias; SEITZ, Thomas; NEWTON, Trevor William; MASSA, Dario; MIETZNER, Thomas; PASTERNAK, Maciej; KREUZ, Klaus; EVANS, Richard Roger; LERCHL, Jens; WO2014/184016; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1303587-99-6, 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 1303587-99-6 as follows.

Synthesis of 2-chloro-8-(3-chlorobenzyl)-7 , 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0455] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (100 mg, 0.58 mmol) in DMF (1 mL) under argon atmosphere was added sodium hydride (27 mg, 1.16 mmol) at 0 C. After stirring for 10 mins, l-(bromomethyl)-3-chlorobenzene (92 mg, 0.70 mmol) was added to the reaction mixture at 0 C and stirred for 1 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford 2-chloro-8-(3- chlorobenzyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (160 mg, 93%) as an off- white solid. 1H-NMR (CD3OD, 400 MHz): delta 7.61 (s, 1H), 7.39-7.22 (m, 4H), 4.52 (s, 2H), 4.20-4.18 (m, 2H), 3.53-3.50 (m, 2H); LCMS: 295.8 (M+1); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 muiotaeta); RT 3.79 min 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 60% EtOAc/hexane (R 0.5).

According to the analysis of related databases, 1303587-99-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics