Month: November 2020

610-97-9, 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. 610-97-9 name is Methyl 2-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.

Methyl 2-iodobenzoate (25 g, 95 mmol), prop-2-yn-1-ol (8.02 g, 143 mmol) and TEA (26.6 ml, 191 mmol) were added to a deareated mixture of Pd(PPh3)4 (0.220 g, 0.191 mmol), copper(I) iodide (0.073 g, 0.382 mmol) in DMF (60 ml). The resulting mixture was stirred at 90C for 5 hrs and then at 40C overnight. The reaction mixture was poured into EtOAc (600 ml) and washed with brine (600 ml). Organic phase wasthen concentrated and the dark oil was rinsed with Et20 (600 ml). The mixture was filtered, and then concentrated to give the title compound as deeply brown oil (13.0 g). This compound was used in the next step without any further purification and characterization.UPLC-MS: 1.53 mi [M+H-18]+. (Method 4)

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

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; BIAGETTI, Matteo; CAPELLI, Anna Maria; ACCETTA, Alessandro; CARZANIGA, Laura; WO2015/91685; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 19094-48-5, name is 3,5-Diiodobenzoic acid, molecular formula is C7H4I2O2, 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. 19094-48-5

S3.ll: To a solution of S3.10 (6.8 g, 18 mmol) in methanol (200 mL) was added sulfuric acid (0.5 mL). The reaction mixture was refluxed for 7.5 hours, then after cooling concentrated and deionized water (200 mL) was added. A dark-brown solid was collected by filtration and purified by column chromatography (silica gel; hexanes:ethyl acetate = 8:2). The product was obtained as a white powder, 4.2 g (59.2%), by recrystallization from methanol/water. NMR (300 MHz, CDC13): delta 8.29 (d, J= 1.6 Hz, 2H), 8.20 (t, J= 1.6 Hz, 1H), 3.90 (s, 13 delta 163.97, 148.99, 137.56, 133.08, 94.32, 52.73.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19094-48-5, its application will become more common.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; ZUNIGA, Carlos; MARDER, Seth; HASKE, Wojciech; KIPPELEN, Bernard; FENG, Daijun; WO2014/11491; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

135050-44-1, The chemical industry reduces the impact on the environment during synthesis 135050-44-1, name is 3-Chloro-4-iodoaniline, I believe this compound will play a more active role in future production and life.

Example 55: N-(5-Chloro-2-( (E)-3-f3-( 4-fluoro-benzvl)-3,8-diaza-bicvclof3.2.110ct-8-vll-3-oxo- propenyl(at)-4-pyrazin-2-yl-phenyl)-acetamide; a) 3-Chloro-4-pvrazin-2-vl-phenylamine; 3-Chloro-4-iodo aniline (0. 349 g; 1.375 mmol ), 2- (tri-n-butylstannyl)pyrazine and (1.015 g; 2.75 mmol) PdC12(PPh3)2 (0.193 g; 0.16 mmol) are dissolved in xylene (5 ml) and refluxed for 2.5 h. The reaction mixture is taken up in TBME and extracted with 2N HCI three times. The combined HC-phases are poured on a saturated solution of saturated Na2C03 and extracted with TBME three times. The combined organic phases are dried over Na2S04, filtered and evaporated to dryness and purified via chromatography (Si02, acetone/hexanes 1/3) to yield the desired product as yellow crystals (162 mg; 57 %). 1 H-NMR (400MHz; DMSO-d6), No. (ppm) : 5.78 (s, 2H) ; 6.62 (dd, 1 H); 6.70 (d, 1H) ; 7.34 (d, 1H) ; 8.50 (d, 1 H); 8.63 (m, 1 H); 9.48 (s, 1 H). MS (m/z) ES+: 206 (MH+).

The chemical industry reduces the impact on the environment during synthesis 3-Chloro-4-iodoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/103054; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 18698-96-9 as follows. 18698-96-9

STR164 Step 1–Preparation of 2-(2-Iodophenyl)ethanol. A solution of o-iodophenylacetic acid (19.87 g, 75.83 mmol) in dry tetrahydrofuran (110 mL) was added dropwise over 41 min to a solution of borane in tetrahydrofuran (151 mL of 1 M solution, ca. 151.0 mmol) which was cooled with an ice-water bath. The reaction was stirred at 0 to 10 C. for 2 hr 15 min. After the reaction mixture was cooled to 0 C., it was quenched by cautious addition (frothing|) of 10 (vol.) % acetic acid in methanol over 20 min. Stirring was continued for 25 min before the reaction was concentrated on a rotary evaporator. The residue was dissolved in ethyl acetate and washed with saturated ammonium chloride followed by saturated sodium bicarbonate. The organics were dried (Na2 SO4) and concentrated to a yellow oil (18.07 g) which was used in the next step without purification. TLC (hexane-ethyl acetate, 1:1): Rf =0.71; 1 H-NMR (DMSO-d6): delta 2.81 (t, J=7.2 Hz, 2H), 3.53 (dt, J=5.1 Hz, 7.5 Hz, 2H), 4.73 (t, J=5.4 Hz, 1H), 6.90-6.95 (m, 1H), 7.29 (dd, J=4.9 Hz, 0.8 Hz, 2H), 7.79 (d, J=7.7 Hz, 1H); MS (EI) 248 [M]+ (C8 H9 IO, FW=248.07).

According to the analysis of related databases, 18698-96-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Corporation; US5886022; (1999); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

626-01-7, 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. 626-01-7, name is 3-Iodoaniline, A new synthetic method of this compound is introduced below.

General procedure: In a 10-ml round-bottom flask equipped with a condenser, a mixture of the aromatic amine (2 mmol), ethyl acetoacetate (1 mmol), and [Pyridinium-SO3H]HSO4 (0.0,385 g, 15 mol %) was stirred at 100 C for 10 min. Afterwards, the aromatic aldehyde (2 mmol) was added, and the resulting mixture was kept under stirring for the specified time in Table 3, the progress of the reaction was followed by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted by the warm EtOAc (10 ml) to separate the catalyst. EtOAc was removed and the crude product was recrystallized from aqueous ethanol (96 %) to afford the pure product, which required no further purification. The recovered catalyst was washed with EtOAc (2 x 10 ml), dried, and reused, without considerable catalytic activity decrease.

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:
Article; Mohammadi, Sedigheh; Abbasi, Mohsen; Research on Chemical Intermediates; vol. 41; 11; (2015); p. 8877 – 8890;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

61203-48-3, 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. 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

[230] b. N-(6,7-Methylenedioxyquinolin-4-yl)-N-[2-(N,N-diethylamino)ethyl]-2- iodo-4,5-dimethoxybenzamide. Oxalyl chloride (1.12 g , 8.8 mmol) was added to a solution of 2-Iodo-4,5-dimethoxybenzoic acid (820 mg, 2.6 mmol; see above) in anhydrous methylene chloride (40 mL) and the stirred mixture was refluxed for 4 hours. The mixture was then concentrated to dryness under reduced pressure. The acid chloride was dissolved in 40 mL of methylene chloride and added to a solution of 4-[[2-(Diethylamino)ethyl]amino]-6,7-methylenedioxyquinoline (640 mg, 2.2 mmol), and triethylamine (2.2g, 22 mmol) in methylene chloride (50 mL) and the resulting mixture was stirred at reflux under nitrogen for 2 hours. The reaction mix was cooled and washed with a saturated solution of sodium bicarbonate (3 x 75 mL), and extracted into dilute HCl (4 x 100 mL). The aqueous extract was then neutralized with 30% NaOH and extracted with CHCl3 (4 x 100 mL), washed with brine (100mL), dried (MgSO4) and evaporated, yielding 1.1 g as a sticky semisolid glue, in 86% yield; 1H NMR (CDCl3) 0.96 (t, 6H, J=7.2), 2.54 (q, 4H, J=7.2), 2.82 (m, 2H), 3.29 (s, 3H), 3.71 (s, 3H), 3.92 (m, 1H), 4.46 (m, 1H), 6.12 (s, 2H), 6.37 (s, 1H), 7.00 (s, 1H), 7.27 (d, 1H, J=4.8), 7.33 (s, 1H), 7.39 (s, 1H), 8.52 (d, 1H, J=4.8); 13C NMR (CDCl3) 11.8, 47.1, 47.5, 50.7, 55.5, 56.1, 82.7, 98.5, 102.2, 106.7, 110.6, 120.1, 121.8, 122.7, 133.7, 146.3, 148.1, 148.3, 148.5, 149.0, 149.7, 151.0, 170.0; HRMS calcd for C25H28O5N31H: 578.1153; found: 578.1153.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; GENZYME CORPORATION; TEICHER, Beverly A.; SCHMID, Steven M.; WO2012/15875; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 76801-93-9, name is 5-Amino-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide, molecular formula is C14H18I3N3O6, 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. 76801-93-9.

5-amino-N,N’-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide (500 g) was taken in N-methylpyrrolidone (500 ml). Chloroacetyl chloride (500 ml) was then added over three hours maintaining the temperature below 35 0C. After addition, the reaction mixture was stirred for three hours at 50 0C. Water (1.3 L) was added to the reaction mass and the precipitated product was filtered, washed and dried. Yield: 97%Purity: 96% (by HPLC)

The synthetic route of 5-Amino-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WOCKHARDT RESEARCH CENTRE; KULKARNI, Dilip, Ganesh; SINHA, Rohit, Kumar; SHINDE, Prakash, Sakharam; SIDDIQUI, Mohammed, Jaweed, Mukarram; ZAKIR, Gafoor, Shaikh; MOHAMMED, Ismail, Shafi; ANIS, Mushtaqe, Ali, Saiyad; KHAN, Nasim; WO2008/104853; (2008); 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. 35944-64-0, name is 3-Iodo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., 35944-64-0

Adapting literature procedures (Jian, et al., U.S. Application Publication No. 2006/173006 and International Application Publication No. WO 2010/039238; Bookster, et al., International Application Publication No. WO 2010/047982), to a solution of commercial 3-iodo-4-methylaniline (1.0 g, 4.30 mmol) in water (25 mL) was added aqueous 0.5 M sulfuric acid (H2SO4) (25 mL, 12.5 mmol). The reaction mixture was heated at ~80C (oil bath) until all solids were dissolved to yield a pale brownish solution. The solution was cooled quickly to ~0C (ice bath) upon which part of 3-iodo-4-methylaniline began to precipitated as crystals. To the reaction mixture was added in small portions solid sodium nitrite (NaN02) (444 mg, 6.39 mmol). After ~2 hours at ~0 C (ice bath), the reaction mixture became a clear yellow solution. Urea (H2NCONH2) (126 mg, 2.1 mmol) was added at this temperature and the solution was allowed to warm gradually to room temperature. Aqueous 0.5 M sulfuric acid (H2SO4) (25 mL, 12.5 mmol) was added and the reaction mixture was heated at reflux for -30 min followed by cooling to room temperature. Extractive aqueous work-up with ethyl acetate and purification bysilica gel column chromatography using an EtOAc/hexane mixture (EtOAc/hexane = 1 :8, v/v) provided the target compound as a deep orange oil. Rf. -0.37 (EtOAc/hexane = 1 :9, v/v). 1H MR (400 MHz, CDC13): delta 7.30 (d, J = 2.0 Hz, 1H), 7.06 (d, J= 8.4 Hz, 1H), 6.72 (dd, J= 8.4, 2.4 Hz, 1H), 4.71 (br. s, 1H) ppm. The analytical data correspond to the data for the compound in the literature. 3-Iodo-4-methyl phenol (l-methyl-2-iodo-4-hydroxybenzene) is also commercially available.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; QUADRIGA BIOSCIENCES, INC.; JANDELEIT, Bernd; FISCHER, Wolf-Nicolas; KOLLER, Kerry J.; RINGOLD, Gordon; (469 pag.)WO2017/24009; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

615-42-9, 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. 615-42-9, name is 1,2-Diiodobenzene, A new synthetic method of this compound is introduced below.

[00150] Copper (I) iodide (FW 190.45, 0.90 grams, 4.72 mmol), 1,10-phenanthroline (FW 180.21, 0.83 grams, 4.62 mmol), cesium carbonate (FW 325.82, 19.00 grams, 58.30 mmol), 1 ,2-diiodobenzene (FW 329.90, 7.50 grams, 22.70 mol), di(ethylene glycol) ethyl ether (FW 134.17, 9.18 grams, 68.40 mol) and 100 milliliters of dry xylene were charged in a 350 milliliter three necked round bottom flask. The reaction mixture was heated with stirring at reflux temperature for 20 hours under nitrogen. The resulting suspension was cooled to room temperature by adding 50 milliliters of toluene. Then reaction mixture was filtered through celite and alumina. The low boiling (xylene and toluene) component was removed by a rotary evaporator and high boiling component di(ethylene glycol) ethyl ether by air bath oven at 200C under high vacuum for 2 hours. The residue was purified by flask chromatography on silica gel. The final dark yellow product yielded 7.00 grams (90%). The product I and C NMR analysis shows the formation of aryl ether product. IR: neat (cm” FontWeight=”Bold” FontSize=”10″ ): 745, 843, 931, 1052, 1 1 16, 1219, 1256, 1325, 1350, 1373, 1453, 1501, 1593, 2869, 2929, 2973. 1H NMR (CDC13): delta 6.76 (m, 4H, Ph), 4.02 (t, 4H, -OCH2-), 3.71 (m, 4H, -CH2O-) 3.57 (m, 4H, -OCH2), 3.45(m, 4H, -OCH2-), 3.37(t, 4H, -OCH2-), 1.06 (t, 6H, -CH3). 13C NMR (CDC13): 149.42, 121.61, 1 15.04, 70.89, 69.89, 69.76, 68.93, 66.59, 15.14.

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; EXXONMOBIL RESEARCH AND ENGINEERING COMPANY; PATIL, Abhimanyu, Onkar; BODIGE, Satish; WO2015/60985; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-39-4, 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. 116632-39-4, name is 5-Bromo-2-iodotoluene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under argon protection, 114.4 g was added to the reaction flask2-iodo-5-bromotoluene(I),46.6 gO-aminothiophenol (II), 2 g of cuprous iodide,146.05 g of cyclohexanediamine and 200 mL of water,Mechanical stirring, oil bath 110 C, the reaction 6 h.The reaction mixture was cooled to room temperature, extracted with 200 mL * 3 ethyl acetate, 100 mL * 3 ammonia water and 100 mL * 3 purified water. The combined ethyl acetate phases were washed with 200 mL of purified water and 60 mL of aqueous ammonia,Wash with brine, dry over anhydrous sodium sulfate. The dried ethyl acetate layer was pulled dry, add 100 mL petroleum ether dissolved, stirred and cooled to -5 ~ -20 C, with a large amount of solid precipitation, filtration, the filter cake was washed with petroleum ether.The filter cake was collected and dried under reduced pressure at 40 C to giveThe yield of 2- (2-methyl-4-bromo-phenylmercapto) aniline (1Pi) was 98.04g with a yield of 85.7% and a purity of 91.3%

The synthetic route of 116632-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Ji Bell Pharmaceutical Co., Ltd.; Ding Deping; Li Zhaoguang; Feng Qi; Tang Zhiqun; Liu Jun; Jiang Bin; (10 pag.)CN107513048; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com