Category: 5922-60-1

Some common heterocyclic compound, 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, molecular formula is C7H5ClN2, 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. name: 2-Amino-5-chlorobenzonitrile

To a mixture of 2- amino-5-chlorobenzonitrile (5.0 g, 32.8 mmol) and hydroxylamine hydrochloride (2.56 g, 36.8 mmol) in water (1 mL) and EtOH (30 mL) was added sodium methoxide (25% wt. soln; 9 mL) and the mixture heated to reflux for 16 hrs. After cooling, 3M NaOH solution was added (75 mL) and the volatiles removed in vacuo. The remaining aqueous phase was washed with DCM, separated and then adjusted to pH~4 by the addition of IN HC1 solution. Filtration and washing of the subsequent precipitate with water gave the N-hydroxybenzimidamide as a colorless solid used 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 5922-60-1, its application will become more common.

Reference:
Patent; INCEPTION 1, INC.; JACINTHO, Jason, Duarte; CLARK, Ryan, Christopher; SHENG, Tao; OBALLA, Renata, Marcella; STOCK, Nicholas, Simon; ROPPE, Jeffrey, Roger; (161 pag.)WO2017/192304; (2017); A1;,
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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 5922-60-1 as follows. Safety of 2-Amino-5-chlorobenzonitrile

General procedure: 2-aminobenzonitrile (1mmol), and KCC-1/IL NPs (0.0007g) were added. The autoclave was closed, purged twice with CO2 gas, pressurized with 0.8MPa of CO2 and then heated at 70C for 60min. Then the reactor was cooled to ambient temperature, and the resulting mixture was transferred to a 50mL round bottom flask. Upon completion, the progress of the reaction was monitored by TLC when the reaction was completed, EtOH was added to the reaction mixture and the KCC-1/IL NPs were separated by distillation under vacuum. Then the solvent was removed from solution under reduced pressure and the resulting product purified by recrystallization using n-hexane/ethyl acetate.

According to the analysis of related databases, 5922-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sadeghzadeh, Seyed Mohsen; Catalysis Communications; vol. 72; (2015); p. 91 – 96;,
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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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5ClN2

2-amino-5-chlorobenzonitrile (152.6 mg, 1.0 mmol) was sequentially added to a 100 mL high pressure sealed tube, benzyl alcohol(129.6 mg, 1.2 mmol, 1.2 equiv.), cesium hydroxide monohydrate (167.9 mg, 1.0 mmol), an air ball was added to the closed tube.Stir at 120 C for 36 h, after monitoring the reaction by TLC or GC-MS,The product was purified by column chromatography. The isolated yield was 65%.

According to the analysis of related databases, 5922-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yangzhou University; Xu Qing; Wang Qi; Lv Miao; Li Yang; Cao Hongen; (16 pag.)CN109879820; (2019); A;,
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Some common heterocyclic compound, 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, molecular formula is C7H5ClN2, 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. SDS of cas: 5922-60-1

Example 3: Synthesis of 6-chloro-2,4-diamino-quinazolineA mixture of 2-amino-5-chlorobenzonitrile (1.07 g, 7.0 mmol), chloro- formamidine hydrochloride (1.6 g, 14 mmol), sulfolane (0.5 ml) and dimethylsulfone(3 g) was heated at 165 0C for 30 minutes. Then, water (30 ml) was added to the reaction mixture. The pH was adjusted to 7-8 by the addition of a 33 percent aqueous ammonia solution in water. The precipitate was collected by filtration, washed with water and dried over P2O5, yielding the title compound as a yellowish solid (1.35 g, yield: 99 percent) which was characterized by its mass spectrum as follows: MS (m/z): 195([M+H]+, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5922-60-1, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2008/9077; (2008); A2;,
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Electric Literature of 5922-60-1, The chemical industry reduces the impact on the environment during synthesis 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: Under a N2 atmosphere, a Schlenk tube was charged with 2-aminobenzonitrile 1 (0.3 mmol),sodium arylsulfinate 2 (0.6 mmol), Pd(OAc)2 (10 mol percent), bpy (20 mol percent), p-NBSA (10 equiv), THF (2 mL), and H2O (1 mL) at room temperature. The reaction mixture was stirred vigorously at 80 °C for 48 h. The mixture was poured into ethyl acetate, which was washed with saturated NaHCO3 (2 × 10 mL) and then brine (1 × 10 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous MgSO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products 3.

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-Amino-5-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Jiuxi; Li, Jianjun; Su, Weike; Molecules; vol. 19; 5; (2014); p. 6439 – 6449;,
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Adding a certain compound to certain chemical reactions, such as: 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, belongs to nitriles-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 5922-60-1, Quality Control of 2-Amino-5-chlorobenzonitrile

1) Synthesis of (2-amino-5-chlorophenyl)cyclopropyl) methanone 2-Amino-5-chlorobenzonitrile (500 mg, 3.28 mmol) was dissolved in THF (10 mL), and while stirring the reaction solution at 0°C, cyclopropyl magnesium bromide (0.5 M THF solution, 26.4 mL) was added dropwise thereto. The reaction solution was stirred overnight under heating at 80°C, followed by ice-cooling, and 2 N hydrochloric acid was added thereto under ice-cooling. After the reaction solution was stirred at room temperature for 2 hours, the solution was diluted with ethyl acetate and then neutralized with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated and washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane = 3/1), whereby (2-amino-5-chlorophenyl) (cyclopropyl) methanone (453 mg, 83percent) was obtained as a yellow solid. 1H-NMR (400 MHz, CDCl3) delta: 0.98-1.03 (2H, m), 1.16-1.20 (2H, m), 2.54-2.60 (1H, m), 6.61 (1H, d, J = 8.8 Hz), 7.21 (1H, dd, J = 8.8, 2.4 Hz), 7.92 (1H, d, J = 2.4 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-5-chlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; EP2210880; (2010); A1;,
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5922-60-1, name is 2-Amino-5-chlorobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C7H5ClN2

N-(4-Chloro-2-cyanophenyl)-2-(5-morpholin-4-ylbenzimidazol-2-yl)acetamide LiHMDS (2.5 equivalents) was added to ethyl 2-[5-(2-morpholin-4-ylethoxy)benzimidazol-2-yl]acetate (1.0 equivalent) in THF at -78° C. After 1 hour, 2-amino-5-chlorobenzenecarbonitrile (0.82 equivalents) in THF was added. The reaction was allowed to warm to 23° C. and stirred overnight. The resulting mixture was quenched with NH4Cl (aqueous saturated solution) and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo to yield a brown solid. The crude material was purified by silica gel chromatography (5:1 EtOAc:hexane) to give the desired product. LC/MS m/z 396.1 (MH+), Rt 1.79 minutes. N-(4-chloro-2-cyanophenyl)-2-(5-morpholin-4-ylbenzimidazol-2-yl)acetamide (1.0 equivalent) was heated in NaOMe (0.5 M in MeOH, 18 equivalents) at 70° C. for 2 hours. The resulting mixture was cooled, and the resulting solid was filtered and washed with water to give the desired product. LC/MS m/z 396.4 (MH+), Rt 2.13 minutes.

The synthetic route of 5922-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chiron Corporation; US2005/261307; (2005); A1;,
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Synthetic Route of 5922-60-1, These common heterocyclic compound, 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, 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.

General procedure: To a solution of 2-cyano-4-chloroaniline 3g (19.6 mmol) in 30 mL of AcOH was added dropwise 1,2 mL (23.6 mmol) of bromine and the resulting mixture was stirred at 50 oC overnight. The resulting precipitate was filtered by suction on a glass frit, washed with H2O and dry under vacuum. The solid was then added by portion to a hot (50 oC) stirred solution of isoamyle nitrite 10 mL in 10 mL of DMF. After 10 min the mixture was cooled to room temperature and poured into 100 mL of HCl 3N, subject to extraction with AcOEt (3 X 40 mL), dry over Na2SO4 and concentrated on a rotary evaporator. Purification of the residue by column chromatography yielded 2.08g (49 %) 9c as a white solid1H NMR (CDCl3), d = 7.50 (t, 1H, J=2.0 Hz, CHAr); 7.60 (t, 1H, J=2.0 Hz, CHAr); 7.65 (t, 1H, J=2.0 Hz, CHAr). 13C NMR (CDCl3), d = 115.6 (1C, Cq); 166.4 (1C, Cq); 123.8 (1C, Cq); 131.0 (1C, CHAr); 133.4 (1C, CHAr).

Statistics shows that 2-Amino-5-chlorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 5922-60-1.

Reference:
Article; Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3243 – 3247;,
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Related Products of 5922-60-1, 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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-amino-5-chlorobenzonitrile (1.00 g, 6.55 mmol) was suspended in ethyl chloroformate (3.1 mL, 33 mmol) and heated to 93 °C. The reaction was carried out for 18 h, cooled to room temperature and then worked up with a saturated solution of sodium bicarbonate and EtOAc. No further purification was required. The reaction yielded an orange solid 1.25 g, 5.56 mmol, 85percent. (Rf = 0.30, 20percent EtOAc/Hex). Mp 136-138 °C. 1H NMR (300 MHz, CDCl3) delta 8.29 – 8.22 (m, 1H, ArH), 7.59 – 7.52 (m, 2H, ArH), 7.13 (s, 1H, NH), 4.29 (q, J = 7.1 Hz, 2H, CH2), 1.36 (t, J = 7.1 Hz, 3H, CH3). 13C NMR (75 MHz, CDCl3) delta 152.68, 139.68, 134.47, 131.44, 128.14, 120.59, 117.64, 115.11, 62.27, 14.37. HRMS: calcd for C10H10N2O2Cl [M+H]+, 225.0431, found 225.0426.

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

Reference:
Article; Brigg, Siobhan; Pribut, Nicole; Basson, Adriaan E.; Avgenikos, Moscos; Venter, Reinhardt; Blackie, Margaret A.; van Otterlo, Willem A.L.; Pelly, Stephen C.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 6; (2016); p. 1580 – 1584;,
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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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Amino-5-chlorobenzonitrile

Add 2-amino-5-chlorobenzonitrile (152 mg, 1 mmol), benzyl alcohol (108 mg, 1 mmol),Fe (NO3) 3 · 9H2O (40.4 mg, 0.10 mmol), TEMPO (15.6 mg, 0.10 mmol),t-BuOK (224mg, 2equiv) and 2mL of toluene were sequentially added to a 25mL reaction tube, and the reaction mixture was reacted under reflux for 12h and cooled to room temperature;Ethyl acetate was added to dilute the reaction solution, and then washed three times with water, and then the organic phase was separated.After drying over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product;The crude product was purified by column chromatography with petroleum ether / ethyl acetate to obtain a pure product with a yield of 74%.

The synthetic route of 5922-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Science and Technology; Li Bindong; Hu Yongke; (12 pag.)CN110357823; (2019); A;,
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