Category: 335349-57-0

Application of 335349-57-0,Some common heterocyclic compound, 335349-57-0, name is 5-Chloro-4-iodo-2-nitroaniline, molecular formula is C6H4ClIN2O2, 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 5-chloro-4-iodo-2-nitroaniline (Intermediate 6, 36.5 g, 122 mmol) in EtOH (800 niL) and water (150 mL) was added iron powder (38 g, 673mmol) and NH4Cl (16 g, 306 mmol). The mixture was heated under nitrogen at 5O0C overnight. Additional iron powder (38 g, 673 mmol) and NH4Cl (16 g, 306 mmol) were added and heating was continued for 45 h. The reaction mixture was cooled, filtered and concentrated. The residue was re-dissolved in ethyl acetate and washed with sodium bicarbonate solution. The organic phase was concentrated to afford the desired product as a gray solid, which was used in the next step 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 5-Chloro-4-iodo-2-nitroaniline, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; METABASIS THERAPEUTICS, INC.; DANG, Qun; CHUNG, De Michael; GIBSON, Tony, S.; JIANG, Hongjian; CASHION, Daniel, K.; BAO, Jianming; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F. Anthony; SEBHAT, Iyassu; WODKA, Dariusz; WO2010/51206; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 335349-57-0, 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. 335349-57-0, name is 5-Chloro-4-iodo-2-nitroaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 5-chloro-4-iodo-2-nitroaniline (Intermediate 1, 36.5 g, 122 mmol) in EtOH (800 mL) and water (150 mL) was added iron powder (38 g, 673mmol) and NEta4CI (16 g, 306 mmol). The mixture was heated under nitrogen at 5O0C overnight. Additional iron powder (38 g, 673 mmol) and NH4Cl (16 g, 306 mmol) were added and heating was continued for 45 h. The reaction mixture was cooled, filtered and concentrated. The residue was re-dissolved in ethyl acetate and washed with sodium bicarbonate solution. The organic phase was concentrated to afford the desired product as a gray solid, which was used in the next step without further purification.

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-4-iodo-2-nitroaniline. I believe this compound will play a more active role in future production and life.

These common heterocyclic compound, 335349-57-0, name is 5-Chloro-4-iodo-2-nitroaniline, 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. SDS of cas: 335349-57-0

To a mixture of 5-chloro-4-iodo-2- nitroaniline 1-5 (31.7 g, 106 mmol) and iron powder (59.0 g, 1060 mmol) in 880 mL ethanol was added a solution OfNH4Cl (28 g, 530 mmol) in 240 mL of water. The resulting mixture was mechanically stirred at 60 C for 40 h. After cooling to rt the mixture was filtered and the filtrate reduced to about 500 mL by rotary evaporation. This filtrate was diluted with 1 L of EtOAc and I L of water, and shaken. The organic layer separated, washed with brine, dried (MgSO4) and evaporated to provide crude product. The crude product was dissolved in 80 mL of EtOAc, diluted with 80 mL of hexanes and injected onto a 330 g column Of SiO2, which was pre-eluted with 33% EtOAc in hexanes. The column was subjected to MPLC eluting at 100 mL/min with 33% EtOAc in hexanes (15 min) and then 50% EtOAc (20 min) to provide 5-chloro-4-iodo-l,2- phenylenediamine 1-6. Impure fractions of residue were resubjected to MPLC on a 330 g column of SiO2 by the same method to provide additional 5-chloro-4-iodo-l ,2-phenylenediamme 1-6 as an amorphous solid. 1H NMR (500 MHz, DMSO-d6): delta 4.77 (s, 2H), 4.91 (s, 2H), 6.66 (S5 IH), 6.93 (s5 IH); LC-MS: calculated for C6H6ClIN2 267.9, observed m/e 269.0 (M + H)+.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; METABASIS THERAPEUTICS, INC.; BOOKSER, Brett, C.; DANG, Qun; GIBSON, Tony, S.; JIANG, Hongjian; CHUNG, De Michael; BAO, Jianming; JIANG, Jinlong; KASSICK, Andy; KEKEC, Ahmet; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F., Anthony; SEBHAT, Iyassu; WILSON, David; WODKA, Dariusz; WO2010/47982; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 335349-57-0, name is 5-Chloro-4-iodo-2-nitroaniline, molecular formula is C6H4ClIN2O2, 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 C6H4ClIN2O2

Compound 2S 2-nitro-4-iodo-5-chloroaniline (2200 g, 7.4 mol) was added to a solution of 7.3 L of dimethylsulfoxide (DMS0) and7.3 L methanol (Mu0H) mixed solution, then add K0H (1040g, 18.4mo 1),Temperature control at 30 C plus finish. And then heated to 60 C reaction 4h, TLC detection reaction is complete, then cooled to room temperature, the reaction solution into 10L of water, Stirred for 15min, filtered, the filter cake washed with water to neutral, drying the compound 3S 3-methoxy-4-iodo-5-nitro-aniline(2100 g, 7.14 mol) Yield 97%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 335349-57-0, its application will become more common.

Reference:
Patent; Shanghai Bide Pharmaceutical Technology Co., Ltd.; Mi Taoran; Huang Liangfu; Lu Qinjie; Zhang Ruihao; Li Xinling; (6 pag.)CN106496037; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 335349-57-0, 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. 335349-57-0, name is 5-Chloro-4-iodo-2-nitroaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound number 301 was prepared as follows. To a solution of 5-chloro-4-iodo-2-nitroaniline (6 g, 20.1 mmol) in dioxane (100 ml) and water (10 ml) which was purged and maintained with an inert atmosphere of nitrogen was added[2,4-bis(trifluoromethyl)phenyl]boronic acid (10.3 g, 40.01 mmol), K3PO4 (8.6 g, 40.70 mmol) and Pd(pph3)4 (2.3 g, 2.04 mmol) at room temperature. The resulting solution was stirred overnight at 95 C. in an oil bath. The resulting mixture was concentrated under vacuum to give a residue, which was purified by a silica gel column, eluting with 2% to 3% ethyl acetate in petroleum ether to produce 4-[2,4-bis(trifluoromethyl)phenyl]-5-chloro-2-nitroaniline as a crude light yellow solid (2.2 g, crude). Next, to a solution of 4-[2,4-bis(trifluoro-methyl)phenyl]-5-chloro-2-nitroaniline (2.2 g, crude) in ethanol (50 ml) was added hydrogen chloride (conc, 1.5 ml) and Zn powder (2.2 g, 33.85 mmol). The resulting solution was stirred for 2 h at 90 C. in an oil bath. The reaction was then quenched by the addition of water (300 ml), adjusted pH to 8 with aqueous sodium carbonate and then extracted with ethyl acetate (3¡Á100 ml). The combined organic layers were washed with brine (200 ml), dried and concentrated under vacuum to produce 4-[2,4-bis(trifluoromethyl) phenyl]-5-chlorobenzene-1,2-diamine as a crude brown solid (1.75 g, crude). Finally, a Solution of 4-[2,4-bis(trifluoromethyl)phenyl]-5-chlorobenzene-1,2-diamine (300 mg, crude) in trifluoroacetic acid (10 ml) and hydrogen chloride (conc, 2 ml) was stirred overnight at 80 C. in an oil bath. The solution was evaporated and dissolved in water (30 ml), adjusted to pH 8 with aqueous sodium carbonate and extracted with ethyl acetate (3¡Á50 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column with 10% ethyl acetate in petroleum ether to produce 6-[2,4-bis(trifluoromethyl)phenyl]-5-chloro-2-(trifluoromethyl)-1H-1,3-benzodiazole as a off-white solid (132.4 mg).

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

Reference:
Patent; MERIAL LIMITED; Meng, Charles Q.; US2013/281392; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 335349-57-0, name is 5-Chloro-4-iodo-2-nitroaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H4ClIN2O2

Compound number 307 was prepared as follows. To a solution of [2-chloro-4-(trifluoromethyl)phenyl]boronic acid (4.5 g, 20.06 mmol) in water (30 mL) and dioxane (200 mL) was added K3PO4 (5.7 g, 26.85 mmol), 5-chloro-4-iodo-2-nitroaniline (4 g, 13.40 mmol) and Pd(PPh3)4 (800 mg, 0.69 mmol) maintained with an inert atmosphere of nitrogen and stirred overnight at 95 C. The resulting mixture was concentrated under vacuum to give a residue, which was purified by a silica gel column with 10% ethyl acetate in petroleum ether to produce 5-chloro-4-[2-chloro-4-(trifluoromethyl)phenyl]-2-nitroaniline as a yellow solid (3 g, 32%). Next, to a solution of 5-chloro-4-[2-chloro-4-(trifluoromethyl)phenyl]-2-nitroaniline (3 g, 8.54 mmol) in ethanol (80 mL) was added hydrochloric acid (2 mL) and Zn powder (3.4 g, 52.3 mmol) in portions. The resulting solution was stirred for 2 h at reflux. The resulting mixture was concentrated under vacuum and dissolved in water (100 ml) adjusted to pH 8 with sodium carbonate and extracted with ethyl acetate (3¡Á100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give the residue, which was purified by a silica gel column with 20% ethyl acetate in petroleum ether to produce 4-chloro-5-[2-chloro-4-(trifluoromethyl)phenyl]benzene-1,2-diamine as brown oil (1 g, 36%). Finally, the solution of 4-chloro-5-[2-chloro-4-(trifluoromethyl)phenyl]benzene-1,2-diamine (100 mg, 0.31 mmol) in TFA (5 mL) and hydrochloric acid (conc, 1 mL) was stirred overnight at 80 C. and quenched with water (100 ml), adjusted pH to 8 with saturated aqueous sodium carbonate and extracted with ethyl acetate (3¡Á50 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column with 10% ethyl acetate in petroleum ether to produce 5-chloro-6-[2-chloro-4-(trifluoromethyl)phenyl]-2-(trifluoromethyl)-1H-1,3-benzodiazole as a white solid (107.8 mg, 87%).

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; MERIAL LIMITED; Meng, Charles Q.; US2013/281392; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 335349-57-0,Some common heterocyclic compound, 335349-57-0, name is 5-Chloro-4-iodo-2-nitroaniline, molecular formula is C6H4ClIN2O2, 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 E6 5-(2-tert.-Butoxy-ethoxy)-4-iodo-2-nitro-phenylamine Prepared from 5-chloro-4-iodo-2-nitro-phenylamine (Example A1) (14.9 g, 50 mmol), 2-tert.-butoxyethanol (29.5 g, 250 mmol) and KOH (3.99 g, 60 mmol) in DMSO (25 mL) at 23 C. according to the general procedure E. Obtained as a yellow solid (14.3 g). MS (ISP) 381 [(M+H)+]; mp 144-146 C.

The synthetic route of 335349-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-la Roche Inc.; US6407094; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com