Month: June 2021

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. 135050-44-1, name is 3-Chloro-4-iodoaniline, A new synthetic method of this compound is introduced below., name: 3-Chloro-4-iodoaniline

3-chloro-4-iodoaniline (15 g, 59 mmol) was dissolvedEthyl [(ethyloxy)methylene]malonate (19 mL, 95 mmol)It was heated at 160 C for 4 hours under a reflux condenser.The condenser was then removed and EtOH evaporated. After one hour,Cool it to rt and cure.Break up and suspend the solid in hexane.The mixture was filtered and the cake was washed several times with hexane.A grey solid (23 g, 91%) was obtained.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BURY, MICHAEL JONATHAN; CASILLAS, LINDA N.; CHARNLEY, ADAM KENNETH; HAILE, PAMELA A.; MARQUIS, JR., ROBERT W.; MEHLMANN, JOHN F.; ROMANO, JOSEPH J.; SINGHAUS, JR., ROBERT R.; WANG, GREN Z.; (142 pag.)TW2018/8946; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), belongs to iodides-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 627-31-6, Product Details of 627-31-6

In a 250 mL single-necked flask, 1.0 g (6.75 mmol) of 2-methylbenzothiazepine, 6.0 g (20.3 mmol, 3 eq) of 1,3-diiodopropane, 40 mL of acetonitrile were added in sequence, under Ar gas protection and magnetic stirring. Under the conditions, the mixture was heated to reflux for 24 h. After the reaction solution was cooled, 50 mL of acetone was slowly added, and solids were precipitated under vigorous stirring, and filtered through a Buchner funnel to obtain 2.65 g of a solid yellow solid.The crude yield was 88.4%. The obtained crude product was recrystallized from ethanol and water (v/v = 1:1) to give 2260 mg of solid powder, intermediate of formula I, yield 75%

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, 1,3-Diiodopropane(stabilized with Copper chip), other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Biological Chip Co., Ltd.; Han Junsong; Cui Lei; Xu Yichun; Yuan Qing; Zhou Jiajing; Yin Jiahui; (15 pag.)CN109796781; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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., Quality Control of 5-Chloro-4-iodo-2-nitroaniline

Step B 4-chloro-5-iodobenzene-1,2-diamine. To a suspension of 5-chloro-4-iodo-2-nitroaniline (36.5 g, 122 mmol) in EtOH (800 mL) and water (150 mL) was added iron powder (38 g, 673 mmol) and NH4Cl (16 g, 306 mmol). The mixture was heated under nitrogen at 50 C. 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.

According to the analysis of related databases, 335349-57-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 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; US2010/81643; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 7425-53-8, name is Ethyl 4-iodobutanoate, 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. Recommanded Product: 7425-53-8

Step b: 4-Dibenzylaminobutyric acid, ethyl ester Mix ethyl 4-iodobutyrate (43.5 g, 0.18 mol), dibenzylamine (35.5 g, 0.18 mol), potassium carbonate (24.9 g, 0.18 mol) and ethanol (114 mL dried over 4A molecular sieves). Reflux for 24 hours then stir at room temperature for 48 hours. Add methylene chloride (100 mL) and filter. Evaporate the filtrate to a residue and purify by silica gel chromatography (methylene chloride) to give the title compound (47 g). 1 H NMR (90 MHz, CDCl3) ppm 3.95 (q, 2), 4.35 (s,4), 2.40 (t, 2), 2.25 (t, 2), 1.75 (q, 2), 1.1 (t, 3).

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

Reference:
Patent; Merrell Dow Pharmaceuticals Inc.; US5194430; (1993); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 3718-88-5, name is 3-Iodobenzylamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H9ClIN

Example 54 This example describes the synthesis of 2-chloro-N6 -(3-iodobenzyl)adenine. A solution of 2,6-dichloropurine (Aldrich Chemical Co., 1 g, 5.3 mmol), 3-iodobenzylamine hydrochloride (1.7 g, 5.8 mmol), and triethylamine (2.2 ml, 15.35 mmol) in ethanol (10 ml) was stirred for 5 days at room temperature. The colorless solid formed was collected by suction, washed with small amount of cold ethanol, and dried to yield 2-chloro-N6 -(3-iodobenzyl)adenine (1.16 g, 60%): m.p. 222-224 C.; mass (EI) 385: 1 H NMR (DMSO-d6 d 4.59 (br s, 2H, –CH2), 7.13 (pseudo t, J=8.2 and 7.5 Hz, 1H, Bn), 7.36 (d, J=7.5 Hz, 1H, Bn), 7.61 (d, J=7.5 Hz, 1H, Bn), 7.74 (s, 1H, Bn), 8.14 (s, 1H, H-8), 8.76 (br s, 1H, exchangeable with D2 O, NH), 13.14 (br s, 1H, exchangeable with D2 O, NH). UV (MeOH) 1max 281.7, 257.5, 232.5 nm.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3718-88-5.

Reference:
Patent; The United States of America as represented by the Department of Health and Human Services; US5773423; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

4897-68-1, name is 1-Bromo-2-iodo-4-methoxybenzene, belongs to iodides-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. COA of Formula: C7H6BrIO

To a flame-dried two-necked flask (100mL) containing a magnetic stirrer, 65 CuI (0.183g, 0.96mmol), 66 dl-pipecolic acid (0.124g, 0.96mmol) and 67 Cs2CO3 (4.18g, 12.80mmol) in 50 68 mLof DMF/69 1,4-dioxane (1/9) was added 70 4-methoxylbenzyl mercaptan (1.07mL, 7.69mmol) and the reaction mixture was stirred at room temperature for 3min 9 4-Bromo-3-iodoanisole (4)(2.0g, 6.41mmol) was then added into the mixture and the resulting solution was heated to 100C and stirred at this temperature for 24h. After cooling to room temperature, the mixture was filtrated through celite and washed with EtOAc (20mL), the organic layer was added saturated 71 aqueous NaCl solution (100mL) and was extracted with EtOAc (50mL×3). The combined organic extracts were dried over anhydrous MgSO4(S). After filtration and removal of solvent, the residue was purified by column chromatography on silica gel using 10/1 (Hexane/EtOAc) as elution to give 11 compound 5 (1.60g, 75%) as a red oil. Rf=0.30 (20:1 Hex/EtOAc); 1H NMR (500MHz, CDCl3) delta 3.72 (s, 3H), 3.79 (s, 3H), 4.10 (s, 2H), 6.58 (dd, J=9.0, 3.0Hz, 1H), 6.78 (d, J=3.0Hz, 1H), 6.85 (d, J=9.0Hz, 2H), 7.29 (d, J=9.0Hz, 2H), 7.41 (d, J=9.0Hz, 1H); 13C{H} NMR (125MHz, CDCl3) delta 37.3, 55.2, 55.4, 112.3, 113.6, 113.9, 114.4, 127.8, 130.0, 133.2, 138.9, 158.9, 159.0; MS (EI, m/z) 340 (M+, 7), 338 (6), 138 (7), 121 (100), 71 (8), 57 (8); HRMS (EI-magnetic sector) m/z: calcd for C15H15BrO2S 339.9956, found 339.9979.

The synthetic route of 4897-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wen, Shi-Ming; Lin, Cheng-Han; Chen, Chin-Chau; Wu, Ming-Jung; Tetrahedron; vol. 74; 20; (2018); p. 2493 – 2499;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 62720-29-0, name is 1,3-Dibromo-5-fluoro-2-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 62720-29-0

Example 102a 2,6-Dibromo-4-fluorobenzaldehyde 102a A solution of 1,3-dibromo-5-fluoro-2-iodobenzene (50 g, 132 mmol) in anhydrous toluene (300 mL) cooled to -35 C. was added the solution of isopropylmagnesium chloride (84 mL, 171 mmol, 2.0 M in diethyl ether) over a period of 30 minutes while maintaining the internal temperature below -25 C. A clear brown solution was obtained. Stirring was continued for 1.5 h. Then anhydrous DMF (34 mL, 436 mmol) was added over a period of 30 minutes. The temperature of the reaction mixture increased to -19 C. The reaction mixture was warmed to 10 C. (room temperature) over 1 h and stirred at this temperature for 1.5 h. The reaction was quenched with saturated aqueous NH4Cl (100 mL), filtered and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography (eluting with petroleum ether/ethyl acetate: from 50:1 to 20:1) to give 102a (20 g, yield 54%) as a yellow solid.

According to the analysis of related databases, 62720-29-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 19718-49-1, 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. 19718-49-1 name is Methyl 4-amino-3-iodobenzoate, 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.

j00292J A round-bottom flask was charged with methyl 4-amino-3-iodobenzoate (7.50 g, 27.1 mmol, 1.00 equiv), DCM (50 mL), triethylamine (7.20 g, 71.3 mmol, 2.63 equiv) and trifluoroacetic anhydride (8.90 g, 42.4 mmol, 1.57 equiv). The resulting solution was stirred overnight at room temperature and washed with water (3 x 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, as described in Example 1, Step 1. The residue was chromatographed on a silica gel column to provide 8.00 g (79% yield) of methyl 3 -iodo-4-(2,2,2-trifluoroacetamido)benzoate as a yell ow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-3-iodobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WEBER, Olivia D.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; WIENER, John J. M.; CISAR, Justin S.; DUNCAN, Katharine K.; (324 pag.)WO2018/217809; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C3H6I2

1,3-dibromopropane (1.0 g, 5 mmol) and NaI (3.0 g, 20 mmol) are added into acetonitrile (35 mL), the reaction is heated to 80 C. under stirring for 3 hours to obtain the crude product of 1,3-diiodopropane. This crude product can be used directly for the next step reaction without any purification. 3,4-pyridine-dicarboximide (740 mg, 5 mmol) and K2CO3 (828 mg, 6 mmol) are added into acetonitrile (20 mL), followed by 1,3-diiodopropane (5 mmol) After heated to 80 C., the reaction proceeds for 16 hours. After completion of the reaction, the reaction solution is filtered, then the filtrate is dried by rotary evaporation to obtain a crude product which is purified by column chromatography to get a yellow solid product, N-(3-iodopropyl)-3,4-pyridine-dicarboximide (200 mg, 13%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 627-31-6.

Reference:
Patent; HANGZHOU BENSHENG PHARMACEUTICAL CO., LTD.; Xu, Rongzhen; Rong, Frank; Xie, Fuwen; Lai, Hongxi; US2013/158068; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 98-61-3, name is 4-Iodobenzenesulfonyl chloride, molecular formula is C6H4ClIO2S, 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. Recommanded Product: 4-Iodobenzenesulfonyl chloride

4-iodobenzenesulfonyl chloride (5.00 g, 16.5 mmol) was added to 250 mL dry three-necked flask and fluorobenzene (7.30 g, 76.0 mmol) was added and stirred.Add anhydrous aluminum chloride (3.31g, 24.8mmol), raise the temperature to 40 ~ 50 C, react 5 ~ 6h, after the reaction is over,Dichloromethane (50 mL) was added to a three-necked flask, dilute hydrochloric acid was slowly added, and stirring was continued until no precipitation was observed.Then, the reaction solution was poured into a separatory funnel, extracted three times with dichloromethane, and then washed with dilute hydrochloric acid for 2 to 3 times until the water layer became colorless.Dry the organic layer over anhydrous sodium sulfate.After filtration, the filtrate was spin-dried in a rotary evaporator to give 4.80 g of a yellow-white solid with a yield of 80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 98-61-3, its application will become more common.

Reference:
Patent; Shenzhen Huaxing Optoelectric Co., Ltd.; Sun Yat-sen University; Li Xianjie; Wu Yuanjun; Lv Boyan; Yu Tao; Huang Qiuyi; Xie Zongliang; Ou Depei; Wang Leyu; Chi Zhenguo; Zhang Yi; Liu Siwei; Xu Jiarui; (15 pag.)CN108101941; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com