Author: Jessica.F

Reference of 4152-90-3,Some common heterocyclic compound, 4152-90-3, name is (3-Chlorophenyl)methanamine, 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.

To a suspension of ethyl 6-brorno-4-hydroxyquinazoline-2-carboxylate (0.891 g, 3 rnrnol) and brornotri(pyrrolidin-1-yl)phosphoniurn hexafluorophosphate (2.10 g, 4.50 rnrnol) in 1,4-dioxane (12 rnl) was added Et3N (1.254 rnl, 9.0 rnrnol). The rnixture was stirred at rt for 3 h and then (3-chlorophenyl)rnethanarnine (0.85 g, 6.0 rnrnol) was added. The rnixture was stirred at rt for another 5 h. The rnixture was poured into hexane/H20 (10 rnL/10 rnL). The solid was filtered and triturated with 3percent EtOAc/hexane and then dried to give ethyl 6-brorno-4-((3- chlorobenzyl)arnino)quinazoline-2-carboxylate (1.2 g, 2.85 rnrnol, 95 percent yield). The rnaterial wasused without further purification. MS (M+H)= 421.

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

Reference:
Patent; STROVEL, Jeffrey William; YOSHIOKA, Makoto; MALONEY, David J.; YANG, Shyh Ming; JADHAV, Ajit; URBAN, Daniel Jason; (334 pag.)WO2017/91661; (2017); A1;,
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Related Products of 20850-43-5, 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. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows.

Taking 10 g about 89.7% content piperazine pyrimidine, 12 g triethylamine, 34 ml isopropanol into 100 ml three port into reaction, stirring at the room temperature under the chlorosilane dropping pepper, in 30 minutes in the transfusion. Heating to 50 C, thermal insulation 4 hours, stirring under cooling to room temperature, filter, recovery mother liquor, in the filter cake by adding 20 ml water beating, filtering, adding 10 ml water washes filters cake. 50 C drying, the crude product shall piribedil 16.6 g, HPLC analysis content 99.2%. Yield 92%

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

Reference:
Patent; Taicang Hongshan Environmental Protection Technology Co., Ltd.; Liu Lu; (9 pag.)CN107216318; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, 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 3972-56-3, Application In Synthesis of 1-tert-Butyl-4-chlorobenzene

General procedure: Alkynyl carboxylic acid (1.0 mmol), aryl chloride (1.0 mmol), Pd(OAc)2 (3.4 mg, 0.015 mmol), L5 (17.5 mg, 0.03 mmol), Cs2CO3 (391 mg, 2.4 mmol), and DMSO (5.0 mL) were added to the reaction vial. The mixture was stirred at 130 °C for 12 h, after which the mixture was extracted with Et2O and the organic layer was dried over magnesium sulfate. Evaporation of the solvent under reduced pressure provided the crude product, which was purified by column chromatography on silica gel.

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

Reference:
Note; Lee, Ju-Hyeon; Raja, Gabriel Charles Edwin; Kim, Jimin; Nam, Kye Chun; Lee, Sunwoo; Bulletin of the Korean Chemical Society; vol. 38; 11; (2017); p. 1368 – 1371;,
Chloride – Wikipedia,
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Related Products 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: In an open-capped cylindrical pyrex-glass (50mL), was added a mixture of an appropriate 2-bromobenzaldehyde (10mmol), proper primary amine (12mmol), TBAA (15mmol), and CDSCS (0.3g, 0.05mol%) in DMSO (10mL) and the mixture was kept at room temperature and irradiated at 60W power (cup horn: 20kHz) in ultrasonic apparatus. The progress of the reaction was monitored by TLC. After completion of the reaction (Table 5), then the reaction mixture was filtered to separate the catalyst and catalyst was washed with EtOAc (3×50mL). The filtrate was then mixed with water (100mL). The separated organic layer was washed with water (2×100mL). Afterward, the organic layer was dried over anhydrous Na2SO4 and evaporated. The crude product was then purified by column chromatography on silica gel eluting with a mixture of n-hexane/EtOAc. 2.2.1 2-Phenyl-2H-indazole (3a) White solid; yield: 1.79g (92%); mp 81-82C; IR (KBr): 3100, 2945, 1652, 1567, 1470cm-1; 1H NMR (250MHz, CDCl3): delta=7.16 (t, 1H, J=7.8Hz), 7.39 (t, 1H, J=7.8Hz), 7.48-7.51 (m, 3H), 7.73 (d, 1H, J=8.5Hz), 7.81-7.86 (m, 2H), 7.97 (d, 1H, J=8.5Hz), 8.46 (s, 1H); 13C NMR (250MHz, CDCl3): delta=118.78, 120.84, 121.07, 121.79, 122.90, 123.34, 127.41, 128.77, 130.12, 141.86, 150.26; MS (EI): m/z (%)=194 (15.7) [M+]; Anal. Calcd for C13H10N2: C, 80.39; H, 5.19; N, 14.42. Found: C, 80.30; H, 5.12; N, 14.49.

The synthetic route of 626-43-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Soltani Rad, Mohammad Navid; Ultrasonics Sonochemistry; vol. 34; (2017); p. 865 – 872;,
Chloride – Wikipedia,
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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. 108-37-2, name is 1-Bromo-3-chlorobenzene, A new synthetic method of this compound is introduced below., Formula: C6H4BrCl

General procedure: General procedure: a 50 mL ask equipped with a magnetic stir bar was charged with aryboronic acid (1 mmol, 1 equiv), aromatic halides (1.2 mmol, 1.2 equiv), catalyst (2 mol%), base (2 mmol, 2 equiv), DMF (5 mL) solution under CO (1 atm) atmosphere, along with sealed the reaction flask by a rubber stopper and CO was injected into it with a stainless steel gas flowmeter. The mixture was then stirred at 120 C forthe indicated time (SI, Fig. S1). After being allowed to cool to roomtemperature, the reaction mixture was diluted with 5 mL water and extracted with diethyl ether (3 × 5 mL). The organic phases werecombined, and the volatile components were evaporated in a rotaryevaporator. The residue was puried by column chromatography onsilica gel.

The synthetic route of 108-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Zheng-Jun; Wang, Xue-Yan; Wang, Xia; Liang, Zhi-Wu; Xu, Xinhua; Catalysis Communications; vol. 101; (2017); p. 10 – 14;,
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Synthetic Route of 61881-19-4, The chemical industry reduces the impact on the environment during synthesis 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, I believe this compound will play a more active role in future production and life.

General procedure: Add sodium acetate, trifluoroethylimidyl chloride (II), hydrazone (III), and 1 mL of organic solvent to the 35 mL Schlenk tube according to the raw material ratio in Table 1.Mix and stir well. After the reaction is completed according to the reaction conditions in Table 2, 2-4 hours,Add elemental iodine, continue the reaction for 1-2 hours, filter, and stir the sample in silica gel.After purification by column chromatography, the corresponding 5-trifluoromethyl-substituted 1,2,4-triazole compound (I) is obtained. The reaction process is shown by the following formula:

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, 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Sci-Tech University; Chen Zhengkai; Hu Sipei; Yang Zuguang; (10 pag.)CN110467579; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2162-98-3,Some common heterocyclic compound, 2162-98-3, name is 1,10-Dichlorodecane, molecular formula is C10H20Cl2, 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 8 20.6 g (0.1 mol) of 4-octylaminopyridine, 10.5 g (0.05 mol) of 1,10-dichlorodecane and 30 ml of white spirit (boiling point 155 to 200 C.) were combined and heated to 130 C. The exothermic reaction causes the temperature to increase to 155 C., and at the same time white crystal precipitate out. The reaction mixture was stirred for a further 4 hours at 140 C., and after cooling to room temperature the very fine crystal sludge was filtered over a filterpaper and washed with petroleum ether, giving a beige, solid mass. The reaction product octenidine dihydrochloride in this example is very difficult to filter off with suction since it is produced in very fine form.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,10-Dichlorodecane, its application will become more common.

Reference:
Patent; AIR LIQUIDE SANTE (INTERNATIONAL); US2001/16660; (2001); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 102-49-8,Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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 stirred solution of tosylate 1 (100 mg, 0.29 mmol) in Acetone or CHCl3 (3 mL) was slowly added amine 2 (0.58 mmol) and ketone 3 (0.87 mmol). Then p-TsOH (25 mg, 0.145 mmol)was addedto the reaction mixture. The resultant mixture was stirred at 60 C for 24 h until the reaction was completed as indicated by TLC. The reaction mixture was concentrated in vacuo, and then extracted with saturated aqueous NaHCO3 and CH2Cl2. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 4 or 5 as syrups.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Dichlorobenzylamine, its application will become more common.

Reference:
Article; Yuan, Wen; Xia, Jianhui; Zhang, Xiaoke; Liang, Peng; Zhang, Jichao; Jiao, Wei; Shao, Huawu; Tetrahedron; vol. 72; 27-28; (2016); p. 3994 – 4000;,
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Electric Literature of 202197-26-0, 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. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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.

Roschangar et al. ,Use of lithium N,O-dimethylhydroxylamide as an efficient in situ protecting agent for aromatic aldehydes. Tertrahedron 2002, 58, 1657-1666). Preparation analogous (Nishino et al.; Process for producing 4-aminoquinazoline compound by chlorination of quinazolin-4-one or its derivative and animation. 2003) as follows: To a mixture of 6-iodo-lH-quinazolin-4-one (10) (6.8Og; 25.0 mmol), toluene (5.0 mL) and POCl3 (27.5 mmol; 2.60 mL) carefully triethylamine (27.5 mmol; 3.81 mL) was added. The mixture was heated to 80 0C for 2 h, cooled to room temperature, a solution of 3-chloro~4-(3- fluorobenzyloxy)phenylamine (15) (27.50 mmol; 6.92 g) in 2~butanone (20.0 mL) added and the mixture stirred at 80 0C for another hour. The mixture was cooled to 00C, the yellow precipitate was filtered off and added to a NaOH solution (IN; 150 mL) by stirring. After 30 min the yellow solid was filtered off, washed with water and a small amount of acetone and dried in vacuo. Yield (8.38 g; 66%) analytical pure sample. 1H-NMR (DMSO-[D6]): delta (ppm) = 5.26 (s, 2H), 7.15-7.22 (m, IH), 7.27 (d, IH, J = 9.1 Hz), 7.29-7.35 (m, 2H), 7.43-7.51 (m, IH), 7.56 (d, IH, J = 8.8 Hz), 7.74 (dd, IH, J = 9.1 Hz, 4J = 2.5 Hz), 8.02 (d, IH5 4J = 2.5 Hz), 8.12 (dd; IH, J = 8.8 Hz, 4J = 1.7 Hz)5 8.62 (s, IH), 8.96 (d, 4J = 1.7 Hz), 9.90 (s, IH, exchangeable).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; 4SC AG; WO2009/63054; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 57946-56-2,Some common heterocyclic compound, 57946-56-2, name is 4-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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 solution of 4-chloro-6-hydroxy-7-methoxyquinoline (3.0 g, 14 mmol) and 4-chloro-2-fluoroaniline (3.5 g, 23 mmol) in cyclohexanol (100 ml) containing 1M ethereal hydrogen chloride (16 ml) was heated at 155 C. for 18 hours.. After cooling the mixture was diluted with ether and isohexanes and the precipitate was collected by filtration.. The crude product was dissolved in a mixture of methylene chloride/methanol/ammonia (100/10/1) and silica (10 g) was added.. The solvent was removed by evaporation and the resulting powder was purified by flash chromatography eluding with methylene chloride/methanol/ammonia (95/5/1 increasing to 80/20/1) to give 4-(4-chloro-2-fluoroanilino)-6-hydroxy-7-methoxyquinoline (1.12 g, 25%). 1H NMR Spectrum: (DMSOd6) 3.95 (s, 3H); 6.30 (m, 1H); 7.25 (s, 1H);7.35 (m, 2H); 7.55 (m, 2H); 8.20 (d, 1H); MS (ESI): 319 [MH]+.

The synthetic route of 57946-56-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.; US6809097; (2004); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics