Tag: M.W=100-200

Electric Literature of 626-43-7,Some common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, 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: The syntheses of the ferrocenyl phenylguanidines were achieved in four steps (Scheme-1 suppl). In the first step; nitrophenylferrocene (a and b) were made by the coupling of ferrocene with diazonium salts of nitroaniline using phase transfer catalyst [20]. In the second step; these nitro phenyl ferrocene were reduced into ferrocenylaniline (c and d) using palladium on charcoal and hydrazine as reducing agent [21]. In the third step three different chloro-substituted thioureas (e) were synthesized by the coupling of substituted aniline with thiocynates in acetone [22]. In the fourth step; the benzoylphenylthiourea (e) were mixed with the ferrocenyl aniline (c and d) in dimethyl formamide (DMF) in equimolar ratio with two equivalents of triethylamine (Et3N). The temperature was maintained below 5C using an ice bath and one equivalent of mercuric chloride (HgCl2) was added to the reaction mixture with vigorous stirring. The ice bath was removed after 30min while the stirring continued overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) till the completion of reaction. Chloroform (CHCl3, 20ml) was added to the reaction mixture and the suspension was filtered through a sintered glass funnel to remove the mercuric sulfide (HgS) residue. The solvents from filtrate were evaporated under reduced pressure and residue was re-dissolved in dichloromethane (CH2Cl2, 20ml), washed with water (4¡Á30ml) and dried the organic phase over anhydrous magnesium sulfate (MgSO4). The solvent was evaporated and residue was purified by column chromatography to afford ferrocenyl phenylguanidines (f and g) [23]. Solid and liquid state characterization data is given in Supplemental part

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloroaniline, its application will become more common.

Reference:
Article; Gul, Rukhsana; Badshah, Amin; Khan, Azim; Junaid, Asif; Rauf, Muhammad Khawar; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 117; (2014); p. 264 – 269;,
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Application of 2613-30-1, 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. 2613-30-1, name is 4-Chloro-2,5-difluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2. Preparation of 1-Bromo-4-chloro-2,5-difluorobenzene Anhydrous copper (II) bromide (2.7 g, 12.1 mmol) and t-butyl nitrite (1.56 g, 15.1 mmol) were combined in anhydrous acetonitrile (25 mL). The resulting mixture was heated to 65 C. and a solution of 4-chloro-2,5-difluoro-phenylamine (1.65 g, 10.1 mmol) in anhydrous acetonitrile (2 mL) was added dropwise (vigorous gas evolution was noted). After the reaction mixture cooled ambient temperature, it was added to 2N HCl and extracted with ether twice. The organic extracts were then combined, washed with 2N HCl, washed with saturated sodium bicarbonate, dried, concentrated and purified by flash chromatography on silica gel (hexanes) to give the title compound as a white solid (1.11 g, 48.4% yield): 1H NMR (CDCl3): delta 7.38 (dd, 2H), 7.21 (dd, 2H).

The synthetic route of 4-Chloro-2,5-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epp, Jeffrey B.; Schmitzer, Paul R.; Guenthenspberger, Katherine A.; Lo, William C.; Siddall, Thomas L.; US2009/62125; (2009); A1;,
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Reference of 108-70-3, 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 108-70-3 as follows.

[PdCl(pi-allyl)]2 (11.6 mg, 0.15 mol %) and cBRIDP (44.4 mg, 0.6 mol %) were placed into a 50 mL, two-necked, round bottomed flask equipped a gas inlet, and the flask was evacuated and filled with nitrogen. Subsequently, to the mixture was added dehydrated THF (8.2 mL, 101.0 mmol, 4.8 equivalents) to prepare a catalyst solution. A 200 mL, four-necked, round-bottomed flask equipped with a Teflon coated magnetic stirring bar, condenser, dropping funnel, thermometer, and a gas inlet was evacuated and filled with nitrogen. Carbazole (10.9 g, 65.0 mmol, 3.09 equivalents) and dehydrated xylenes (66 mL) were charged into the flask, and the mixture was cooled to 5C using an ice bath. Subsequently, to the mixture was added a THF solution of MeMgCl (3.22 mol/L, 20.0 mL, 64.4 mmol, 3.06 equivalents) dropwise via the dropping funnel at such a rate that the temperature of the reaction solution was kept at 20C or lower, and then the dropping funnel was washed with dehydrated xylenes (1 1 mL). Subsequently, to the solution were added 1,3,5-trichlorobenzene (3.8 g, 21.0 mmol, 1.0 equivalent) and the catalyst solution (8.2 mL) successively, and the solution was stirred for 10 minutes under reflux. To the reaction mixture was added an aqueous solution of ammonium chloride, and the mixture was poured into chloroform (1 ,200 mL). The aqueous layer was separated off, and the organic layer was passed through a silica gel pad and concentrated to remove the excess chloroform under reduced pressure. To the thus-obtained suspension was added methanol (200 mL), and the crystal was collected from the suspension by suction filtration, washed with methanol and dried under reduced pressure to afford 11.4 g of tCP as a white powder. Isolated yield: 94.6%. 1H NMR (300 MHz, CDC13): 7.34 (ddd, J = 0.9, 6.9, 7.8 Hz, 6H), 7.48 (ddd, J = 1.2, 7.2, 8.4 Hz, 6H), 7.67 (d, J = 8.1 Hz, 6H), 7.96 (s, 3H), 8.17 (d, J = 7.8 Hz, 6H). 13C NMR (75 MHz, CDC13): 109.7, 120.6, 120.7, 123.5, 123.9, 126.4, 140.3,140.8.

According to the analysis of related databases, 108-70-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKASAGO INTERNATIONAL CORPORATION; NAKAYAMA, Yuji; KOBAYASHI, Tohru; WO2013/32035; (2013); A1;,
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Related Products of 33786-89-9, 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. 33786-89-9, name is 5-Chloro-m-phenylenediamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-chloro-1,3-phenylenediamine (15.0 g, 0.105 mol) in 70 mL ethanol was added ethyl 4,4,4-trifluoroacetoacetate (20.4 g, 0.111 mol), then the mixture was heated at reflux for 18 h. The solvent was removed under reduced pressure until the product began to precipitate. The material was allowed to crystallize for 2 h, whereupon it was filtered and rinsed with cold ether to afford 10.9 g (37%) of 5-amino-7-chloro-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one, a tan solid. The filtrate was concentrated until solid began to precipitate and afforded an additional 3.0 g (10%). 1H NMR (400 MHz, acetone-d6) delta11.0 (broad s, 1H), 9.64 (s, 1H), 7.42 (t, 1H, J=8.1), 6.99 (d, 1H, J=8.1), 6.90 (s, 1H), 6.79 (d, 1H, J=8.1).

The synthetic route of 5-Chloro-m-phenylenediamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US2002/183314; (2002); A1;,
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Synthetic Route of 29671-92-9, These common heterocyclic compound, 29671-92-9, name is Carbamimidic chloride 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.

A l l three-neck round-bottom flask equipped with a mechanical stirrer, a condenser, and a thermocouple was charged with ethyl 2-(6-amino-2,3-dichlorobenzylamino)acetate of formula (3B) (20.00 g, 72.0 mmol), chloroformamidine hydrochloride (12.44 g, 108 mmol) and acetonitrile (120 ml) under argon, and the suspension was heated to 40C. Then, acetic acid (21 ml, 363 mmol) was added and the suspension was heated to reflux (90C in oil bath). After 5 hours, the compound of formula (3B) was fully consumed as checked by HPLC. The suspension was diluted with acetonitrile (60 ml), and then N,N-diisopropylethylamine (44 ml, 252 mmol) was added drop-wise over approx. 3 minutes, and the suspension was stirred for an additional 75 minutes. Then, the reaction mixture was cooled to 50C and water (150 ml) was added. Stirring at 50C was continued for 1 hour. Then, the suspension was filtered, washed with water (30 ml), ethanol (50 ml), and methyl i-butyl ether (50 ml), and dried (23C, 100 mbar, N2 bleed, 18 hours) to give 13.48 g of anagrelide as a pale beige solid (73% of theory) in 99.53% purity (HPLC, external standard)).

Statistics shows that Carbamimidic chloride hydrochloride is playing an increasingly important role. we look forward to future research findings about 29671-92-9.

Reference:
Patent; SYNTHON BV; GIELING, Reinerus Gerardus; LINDEN van der, Johannes Bastiaan; VERKERK, Pascal Renart; MEL?A, Petr; WO2014/139572; (2014); A1;,
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Application 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.

To a solution of phenol A4 (80 mg, 0.22 mmol, 1.0 equiv) indry CH3CN (4 mL) was added tetrabutylammonium hydrogen sulfate (16.0 mg, 0.05 mmol, 0.21 equiv) and powdered NaOH (32 mg, 0.80 mmol, 3.6 equiv). This mixture was then allowed to stir at room temperature for 30 minutes, at which point 1-Amino-3-chloropropane hydrochloride (58 mg, 0.45 mmol, 2.0 equiv) was added to the solution. The mixture was then placed in an oil bath that had been preheated to 55 C, and was allowed to stir at this temperature for 14 hours.Following determination of reaction completion by TLC and LCMS analysis, the solution was then removed from the oil bath and allowed to cool to room temperature. Upon cooling, the mixture was diluted with EtOAc (20 mL) prior to the addition of H20 (10 mL), which served to dissolve all of the inorganic solids present. Following separation of the layers, the aqueous layer was extracted with EtOAc (20 mL). The organic layer was then washed with brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified through flash column chromatography (12 g silica gel cartridge, 0-100% EtOAc/Hexanes, followed by 0-20% MeOHICH2C12, and desired product eluted during 20%MeOH, to yield the desired product (65.0 mg, 70%) as a yellow solid. ?H NIVIR (400 MHz,CHLOROFORM-d) 7.13 (d, J= 8.52 Hz, 2H), 6.85 (d, J = 8.52 Hz, 2H), 3.96-4.13 (m, 2H),2.94 (t, J = 6.70 Hz, 2H), 2.67-2.89 (m, 1H), 2.20 -2.28 (m, 2H), 2.09 -2.15 (m, 1H), 1.91 -2.04 (m, 8H), 1.66 – 1.86 (m, 12H), 1.50 – 1.66 (m, 1H), 1.22 – 1.49 (m, 2H); 13C NMR (100IVIHz, CHLOROFORIVI-d) 157.4, 138.1, 127.8, 114.5, 111.5, 109.3, 76.8, 66.0, 42.5, 41.2,39.3, 36.9, 36.6, 36.5, 35.0, 35.0, 34.9, 34.9, 34.3, 33.2, 32.7, 27.0, 26.6, 23.7; MS (ESI)calculated for C25H36N04 [M + H] m/z 414.26, found 414.17

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; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; TALUKDER, Poulami; RENSLO, Adam, Robert; BLANK, Brian, Richard; MUIR, Ryan, Keith; EVANS, Michael, John; (270 pag.)WO2019/5977; (2019); A1;,
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Electric Literature of 1435-44-5, 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. 1435-44-5 name is 1-Chloro-2,4-difluorobenzene, 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.

1-Chloro-2,4-difluoro-5-nitrobenzene: To a stirred solution of 1-chloro-2,4-difluorobenzene (0.829 g, 5.58 mmol, Aldrich, used as received) in conc. H2 SO4 (8.0 mL) at 0 C., KNO3 (0.565 g, 5.59 mmol) was added in one lot. The resulting solution was allowed to warm to 28 C. and stirred overnight at 28 C. It was then poured into ice (80 g) and extracted with ethyl acetate (75 mL). The ethyl acetate was dried over anhydrous Na2 SO4, removed under vacuum, and the resulting oil was dried further under vacuum to afford 1.007 g (93%) of the pure (1 H NMR) title compound as a light red oil; 1 H NMR (CDCl3): delta7.168 (dd, 1H, J1 =9.9 Hz, J2 =8.4 Hz), 8.238 (t, 1H, J=7.5 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Chloro-2,4-difluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and the University of Oregon, Eugene Oregon; Acea Pharmaceuticals, Inc.; The Regents of the University of California; US5631373; (1997); A;,
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Related Products of 112581-77-8, 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. 112581-77-8, name is 2,6-Dichloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Zinc chloride (2.04 g, 15.0 mmol) was dried at 180C for 2 hours under vacuum and then cooled to room temperature, and anhydrous tetrahydrofuran (20.0 mL) was added thereto. n-Butyl lithium (1.6 M, 9.0 mL, 14.4 mmol) was added dropwise thereto over about 30 minutes under ice-cooling and stirred for 30 minutes under ice-cooling, to prepare a solution of n-butylzinc chloride in tetrahydrofuran. Separately, a suspension of 2,6-dichloroimidazo[1,2-b]pyridazine (1.88 g, 10.0 mmol) and [1,3-bis(diphenylphosphino)propane]nickel (II) dichloride (0.16 g, 0.30 mmol) in anhydrous tetrahydrofuran (20.0 mL) was prepared under a nitrogen atmosphere, and the previously prepared solution of n-butylzinc chloride in tetrahydrofuran while being maintained at 3 to 6C was added dropwise thereto over 30 minutes. The mixture was stirred for 15 minutes under ice-cooling and for 3 hours at room temperature, then poured into a saturated saline solution and adjusted to pH 2 with dilute hydrochloric acid. The reaction solution was extracted twice with ethyl acetate, and the extracts were combined, dehydrated over anhydrous magnesium sulfate and concentrated under reduced pressure. The residues were purified by silica gel column chromatography (ethyl acetate : hexane = 1 : 4), to give the title compound as pale yellow crystals. The yield was 2.03 g (96.8%). mp 61.0-63.0C1H NMR (CDCl3, delta): 0.96(3H, t, J=7.3 Hz), 1.41(2H, tq, J=7.5, 7.3 Hz),1.73(2H, tt, J=7.8, 7.5 Hz), 2.81(2H, t, J=7.8 Hz), 6.96(1H, d, J=9.4 Hz), 7.74(1H, d, J=9.4 Hz), 7.79(1H, s). IR(Nujol, cm-1): 3115, 3061, 1545, 1466, 1378, 1326, 1276, 817.

The synthetic route of 2,6-Dichloroimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Takeda Agro Company, Limited; EP1466527; (2004); A1;,
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Reference of 13078-79-0, 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 13078-79-0 as follows.

Example S15; Preparation of (4-tert-butyl-benzyl)-[2-(3-chloro-phenyl)-ethyl]-amine; 0.38 ml of 4-tert-butylbenzaldehyde (2.25 mmol) and 0.215 ml 2-(3-chloro-phenyl)-ethylamine (1.5 mmol) were dissolved in 4.5 ml methanol at rt, and after stirring for 30 min at rt, were refluxed for 2.5 h. After cooling down to rt, 85 mg (2.25 mmol) sodium borohydride were added and after stirring for 5 min at rt, the reaction mixture was then refluxed for 4 h. After cooling down to rt, the reaction mixture was treated with 4 drops 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:2) to give 465 mg light yellow oil (100%). MS (ISP) 302.3 (M+H)+.

According to the analysis of related databases, 13078-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Conte-Mayweg, Aurelia; Kuehne, Holger; Luebbers, Thomas; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2006/30613; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6940-78-9, name is 1-Bromo-4-chlorobutane, 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 6940-78-9, Quality Control of 1-Bromo-4-chlorobutane

In a round bottom flask, 5.0 g of 7-hydroxyquinolin-2(1H)-one, 6.42 g K2CO3 and 25 ml acetone were taken and stirred for 30 minutes at 25-35 C. 5.89 g 1-bromo-4-chloro butane was added into the reaction mixture and stirred for 5-6 hours at 50-55 C. After completion of the reaction, the reaction mixture was cooled to 25-35 C. The reaction mixture was filtered. The solvent was removed by distillation under vacuum. The solid was dried in a hot air oven at 45-50 C. to obtain 7-(4-chlorobutoxy) quinolin-2(1H)-one. Yield: 85%.

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; CADILA HEALTHCARE LIMITED; DESAI, Sanjay Jagdish; PARIHAR, Jayprakash Ajitsingh; SHAH, Alpesh Pravinchandra; (21 pag.)US2017/320862; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics