Month: November 2020

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. 101-79-1, name is 4-(4-Chlorophenoxy)aniline, A new synthetic method of this compound is introduced below., 101-79-1

A solution of 4-tert-butyl-2-aminopyridine (0.177 g, 1.18 mmol, 1 equiv.) in 1.2 mL of anh. CH2Cl2 (1.2 mL) was added to CDI (0.200 g, 1.24 mmol, 1.05 equiv) and the mixture was allowed allowed to stir under argon at room temperature 1 d. To the resulting solution was added 4-(4-chlorophenoxy)aniline (0.259 g, 1.18 mmol, 1 equiv.) in one portion. The resulting mixture was stirred at room temperature for 1 d, then was treated with a 10percent citric acid solution (2 mL) and allowed to stir for 1 h. The resulting organic layer was extracted with EtOAc (3*5 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The resultant residue was treated with CH2Cl2 (10 mL) and a 1N aqueous NaOH solution. This mixture was allowed to stir overnight. The resulting organic layer was extracted with CH2Cl2 (3*5 mL). The combined organic layers were (MgSO4) and concentrated in vacuo. The resultant solids were suspended in diethyl ether (10 mL) and sonicated for 15 minutes. The resulting white solid were dried to give N-(4-tert-butylpyridyl)-N’-(4-(4-chlorophenoxy)phenyl) urea (42 mg, 9percent): mp 198-199¡ã C.

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; BAYER CORPORATION; US2002/165394; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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. 1871-57-4

Sodium hydride (992.6 mg, 60% in mineral oil, 24.8 MMOL) was added portionwise to a solution of (2-hydroxy-ethyl)-carbamic acid test-butyl ester (2 g, 12.4 MMOL) in 1-methyl-2- pyrrolidinone (20 ML) AT-2 C, in order to maintain the temperature BELOW 5 C. The mixture was then stirred for 30 minutes, cooled TO-5 C, and a solution of 3-chloro-2-chloromethyl- 1-propene (1.44 ml, 12.4 MMOL) in 1-methyl-2-pyrrolidinone (10 ml) added dropwise in order to maintain the temperature below 3 C. Once addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for a further 18 hours. The reaction mixture was diluted with water and extracted with ether (2X50 ml). The combined organic extracts were dried over magnesium sulphate and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using ethyl acetate: pentane (10: 90) to give the title compound as a clear oil, 713 mg. H NMR (400MHZ, CDCI3) : No. 1. 46 (s, 9H), 3.51 (d, 2H), 3.72 (d, 2H), 4.00-4. 20 (m, 4H), 4.95 (s, 1H), 5.04 (s, 1H). APCI M/Z 236 [MNA] +

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1871-57-4, its application will become more common.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/74291; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 41965-95-1 as follows. 41965-95-1

Methyl 2-chloro-4-[(3-chloro-4-methoxybenzyl)amino]-6-cyanoquinoline-3-carboxylate, 14 To a heterogenous mixture of quinoline 13 (3.56 mmol) and 3-chloro-4-methoxy benzylamine.HCl (3.92 mmol) in NMP (15 mL) was added iPr2NEt (8.90 mmol). The reaction mixture was heated to 80 C. for 3 h. Subsequently, cooled the reaction mixture to ambient temperature and added 1M aqueous HCl and EtOAc. The resulting layers were separated and the organic layer washed with water (3*) followed by brine (1*). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in a minimum amount of hot EtOAc and allowed to cool to ambient temperature. Hexanes was then added to the solution and the intermediate 14 (80% yield) precipitated out and was collected by vacuum filtration. 1H NMR (300 MHz, CDCl3) delta8.20 (s, 1H), 7.95 (d, 1H, J=8.4 Hz), 7.82 (d, 1H, J=7.5 Hz), 7.38 (s, 1H), 7.27-7.22 (m, 1H), 6.98 (d, 1H, J=8.4 Hz), 6.26 (s, 1H), 4.54 (d, 2H, J=4.8 Hz), 3.95 (s, 3H), 3.93 (s, 3H).

According to the analysis of related databases, 41965-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; Landry, Donald W.; Deng, Shixian; Arancio, Ottavio; Fiorito, Jole; Wasmuth, Andrew; (41 pag.)US10626113; (2020); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, molecular formula is C8H8Cl2N2, 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. 1127-85-1

EXAMPLE XIV STR44 A mixture of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline ?prepared according to the procedure described by M. Botta et al., 40, Tetrahedron, (1984), 3313! (500 mg, 2.4 mmol), phenylhydrazine (270 mg, 2.5 mmol) and N,N-diisopropylethylamine (1 ml, 5.7 mmol) in THF (50 ml) was heated at reflux temperature overnight. The reaction was cooled to room temperature and phosgene (200 ml, 20% in toluene) was added slowly and stirred for an additional 10 min. The mixture was poured into water and extracted with ethyl acetate (3*50 ml). The combined organic layers were washed with brine, dried over Na2 SO4 and evaporated under reduced pressure. The residue was triturated with ethanol and filtered to afford 5-chloro-2-phenyl-7,8,9,10-tetrahydro-1,2,4-triazolo[4,3-c]quinazolin-3-one, m.p. 205-207 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1127-85-1, its application will become more common.

Reference:
Patent; Neurogen Corporation; US5677309; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 328-84-7, name is 3,4-Dichlorobenzotrifluoride, molecular formula is C7H3Cl2F3, 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. 328-84-7.

Example- 1; N-methylpyrrolidone (1050 ml) was charged in an autoclave along with 102 g anhydrous activated potassium fluoride, 377 g 3,4- dichlorobenzotrifluoride was added. Ammonia (158 g) gas was passed in the reactor from the pressure pot at ambient temperature. The content of the reactor was heated to 245-250¡ãC over a period of 2 hours to get reactor pressure of 30-32 kg/cm2. Excess NH3 was fed from the pressure pot to maintain the reactor pressure at 38-40 kg/cm at 245-250¡ãC liquid temperature. Reaction mixture was maintained at 245-250¡ãC and at 38-40 kg/cm2 pressure for further 8 hours. Reaction mixture was cooled to ambient temperature and NH3 was vented and recovered. Reaction mixture was filtered and on fractionation gave 77percent yield of 2-chloro-4- trifluoromethylaniline and 13percent yield of 2-chloro-5-trifluoro methyl aniline based on consumed 3,4-dichlorobenzotrifluoride.

The synthetic route of 3,4-Dichlorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GHARDA, Keki Hormusji; WO2011/107998; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, 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. 108-37-2 name is 1-Bromo-3-chlorobenzene, 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.

0.72 g (29.6 mmol) of magnesium dust was immersed in 15 mL of anhydrous tetrahydrofuran, and one iodine was added thereto, and two drops of m-chlorobromobenzene were added dropwise at room temperature. The turbidity was changed by the air gun micro-heating system, and the system was slightly boiled and dropped into 15 mL of tetrahydrofuran and 5.61 g.A mixture of (29.3 mmol) m-bromochlorobenzene was heated and refluxed for 3 hours after the dropwise addition. Decrease to room temperature and use until the next step. To a solution of the format reagent in tetrahydrofuran, 0.34 g (1.8 mmol) of cuprous iodide was added, and the mixture was stirred at room temperature for 1 hour. Slowly drip propargyl alcohol0.66 g (11.7 mmol), after completion of the dropwise addition, was heated to reflux for 24 hours. After cooling, a saturated ammonium chloride solution was added dropwise to adjust pH = 5. Extracted 3 times with 30 mL of ethyl acetate, combined organic phase, washed with saturated sodium hydrogen carbonate solution, washed with saturated sodium chloride solution, anhydrousDry over sodium sulfate. After spin-drying, 10 mL of methanol was added to the system to precipitate a solid, and the solid was taken out and distilled under reduced pressure to give 1.84 g of a pale yellow oily liquid. The yield was 92.3%.

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

Reference:
Patent; Hebei University of Science and Technology; Zhang Guogang; Du Wei; Zhao Yanli; Feng Xue; Song Miaomiao; Song Wei; Yang Ying; (11 pag.)CN108484535; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13726-14-2, 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 13726-14-2 as follows.

General procedure: Procedure B: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 13726-14-2, and friends who are interested can also refer to it.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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 94-97-3, 94-97-3

A mixture of 5-chloro-1H-benzotriazole (8 g), chloroacetone (6.5 mL), potassium carbonate (9.5 g) and potassium iodide (0.5 g) was stirred in acetone (90 mL) at room temperature for 48 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to give a residue that was purified by chromatography (SiO2, heptane/EA) to afford 1-(5-chloro-2H-benzotriazol-2-yl)-propan-2-one as clear oil [1.8 g, 16%, Rf=0.6 (1:1 EA/heptane)]. The two other regioisomers were also isolated, 1-(6-chloro-1H-benzotriazol-1-yl)-propan-2-one [3.8 g, 35%, Rf=0.45 (1:1 EA/heptane)] and 1-(5-chloro-1H-benzotriazol-1-yl)-propan-2-one [3.2 g, 29%, Rf=0.35 (1:1 EA/heptane)].

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, 5-Chloro-1H-benzo[d][1,2,3]triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Soll, Mark David; Hir de Fallois, Loic Patrick Le; Huber, Scot Kevin; Lee, Hyoung Ik; Wilkinson, Douglas Edward; Jacobs, Robert Toms; Beck, Brent Christopher; US2010/125089; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life. 13918-92-8

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

The chemical industry reduces the impact on the environment during synthesis 13918-92-8. I believe this compound will play a more active role in future production and life.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

112-26-5, 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. 112-26-5 name is 1,2-Bis(2-chloroethoxy)ethane, 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.

3-Nitro-2-naphthol20 W. Woodcock and D.R. Clifford, J. Chem. Soc. (1957), pp. 4139-4141.20 (1.3 g, 6.6 mmol), 1,8-dichloro-3,6-dioxaoctane (0.5 mL, 3.3 mmol), and K2CO3 (1.4 g) in 2 mL of DMF was heated at 115 C for 4 h. After water addition, the reaction mixture was extracted threefold with chloroform. Pure oily product was obtained with the use of column chromatography. As an eluent, methylene chloride (at the beginning) and then a mixture of methylene chloride-acetone (5:1) was used. Yield 0.9 g (57%) of yellow oil. TLC (methylene chloride-acetone, 50:1) Rf=0.55. 1H NMR (CDCl3), delta [ppm]: 3.74 (4H, s); 3.93 (4H, t, J=4.7 Hz); 4.40 (4H, t, J=4.7 Hz); 7.52 (2H, t, J=7.1 Hz); 7.64 (2H, t, J=7.3 Hz); 7.66 (2H, s); 7.90 (2H, d, J=8.2 Hz); 8.01 (2H, d, J=8.2 Hz); 8.40 (2H, s). IR (film): 3060; 2928; 2876; 1632; 1603; 1529; 1447; 1359; 1258; 1229; 1185; 1126; 1071; 953; 900; 869; 752; 476 cm-1. HRMS (EI): [M]+=492.15288 calculated for C26H24N2O8 492.15327.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Bis(2-chloroethoxy)ethane, and friends who are interested can also refer to it.

Reference:
Article; Wagner-Wysiecka, Ewa; Rzymowski, Tomasz; Fonari, Marina S.; Kulmaczewski, Rafa?; Luboch, Elbieta; Tetrahedron; vol. 67; 10; (2011); p. 1862 – 1872;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics