Category: 33348-34-4

Application of 33348-34-4, A common heterocyclic compound, 33348-34-4, name is 4-Amino-3-iodobenzonitrile, molecular formula is C7H5IN2, 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.

In an oven-dried three-necked round bottom flask provided with a reflux condenser was 4-Amino-3-benzonitrile (1.0 g, 4.1 mmol) dissolved in anhydrous THF (10 ml) under N2. BH3-THF was added dropwise. Once the addition was complete the reaction mixture was refluxed for 2h. The mixture was allowed to cool and HCl (2.0 N aq.) (6.0 ml) was added dropwise. Then the mixture was refluxed for 1.0 h. The solvents were removed under vacuum and residue was suspended in CH2Cl2 (30 ml). DMAP (100.1 mg, 0.8 mmol), Et3N (1.3 ml, 9.4 mmol) and BoC2O (2.7 g, 12.3 mmol) were added and the mixture stirred at r.t. for 1.5 h. H2O was added and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography (CH2Cl2ZMeOH 99:1) affording 1.0 g (71%) of the title compound. 1H NMR (CDCl3) delta 7.55 (d, IH), 7.07 (dd, IH), 6.70 (d, 1 H), 4.76 (bs, IH),4.15 (d, 2H), 4.08 (bs, 2H), 1.46 (s, 9H).

The synthetic route of 33348-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIRATORIUS AB; JOHANSSON, Martin; THORNQVIST-OLTNER, Viveca; TOFTERED, Joergen; WENSBO, David; DALENCE, Maria; WO2010/97410; (2010); 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. 33348-34-4, name is 4-Amino-3-iodobenzonitrile, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

To a round bottomed flask equipped with an addition funnel, thermometer, reflux condenser, and nitrogen inlet were added 4-cyano-2-iodoaniline (7.88 g), acetonitrile (24 ml_), and triethylamine (4.5 ml_). Trifluoroacetic anhydride (5.0 ml.) was added to the suspension while maintaining the temperature below 35-40 0C. Note: exothermic addition is addition-rate controlled. The reaction was stirred for 30 min, diluted with water (31.5 ml_). Note: initial portion of addition is exothermic and is addition-rate controlled. The slurry was held at 15-200C for 60 min. The product was isolated by filtration. The solid was washed with 80% aqueous acetonitrile, and dried in vacuo to give the title compound as a colorless solid (9.9 g); 1H NMR (300 MHz, CDCI3) delta 8.49 (1 H, br s), 8.45 (1 H, d), 8.15 (1 H, s), 7.75 (1 H, d)

The synthetic route of 33348-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/127678; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 33348-34-4, name is 4-Amino-3-iodobenzonitrile, 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 33348-34-4, HPLC of Formula: C7H5IN2

General procedure: An oven-dried flask was charged with o-iodoaniline (13 mmol), the corresponding benzyl bromide(10 mmol), NaHCO3 (20 mmol), and DMF (20 mL). The mixture was stirred at 50 C under air for 3-4 h.After the completion of the reaction (monitored by TLC), the reaction mixture was cooled to ambienttemperature and 15 mL water was added to the mixture, then extracted by EtOAc for 3 times (3 ¡Á 30 mL).The combined extracts were washed with brine, dried over Na2SO4, and the solvent was removed in vacuoto provide a crude product, which was purified by column chromatography on silica gel to afford pure product.

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, 4-Amino-3-iodobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Zhengkai; Li, Hongli; Cao, Gangjian; Xu, Jianfeng; Miao, Maozhong; Ren, Hongjun; Synlett; vol. 28; 4; (2017); p. 504 – 508;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 33348-34-4, A common heterocyclic compound, 33348-34-4, name is 4-Amino-3-iodobenzonitrile, molecular formula is C7H5IN2, 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.

INTERMEDIATE 143 – PREPARATION of 3-(2-hydroxyethyl)-2-(triethylsilyl)-1 H-indole-5- carbonitrile; 4-amino-3-iodobenzonitrile (1.65 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (1.57 ml 7.44 mmol), Bis(diphenylphosphino)ferrocene]palladium(ll) chloride (0.276 g; 0.338 mmol), lithium chloride (0.287 g; 6.76 mmol), sodium carbonate (1.43 g; 13.52 mmol) in DMF (14 ml.) was stirred at 100 0C for 15 hours. The solution was filtered through celite, diluted in ethyl acetate, washed with brine and sodium thiosulphate, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 20 % ethyl acetate in heptane) to yield 0.873 g (43%) of the title compound as a yellow solid. ESI/APCI(+):301 (M+H); ESI/APCI(-):299 (M-H).

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; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U. LEUVEN R&;D; reMYND; GRIFFIOEN, Gerard; VAN DOOREN, Tom; ROJAS DE LA PARRA, Veronica; MARCHAND, Arnaud; ALLASIA, Sara; KILONDA, Amuri; CHALTIN, Patrick; WO2010/142801; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 33348-34-4, name is 4-Amino-3-iodobenzonitrile, 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. Product Details of 33348-34-4

tert-Butyl 4-amino-3-iodobenzylcarbamate In an oven-dried three-necked round bottom flask provided with a reflux condenser was 4-Amino-3-benzonitrile (1.0 g, 4.1 mmol) dissolved in anhydrous THF (10 ml) under N2. BH3.THF was added dropwise. Once the addition was complete the reaction mixture was refluxed for 2 h. The mixture was allowed to cool and HCl (2.0 N aq.) (6.0 ml) was added dropwise. Then the mixture was refluxed for 1.0 h. The solvents were removed under vacuum and residue was suspended in CH2Cl2 (30 ml). DMAP (100.1 mg, 0.8 mmol), Et3N (1.3 ml, 9.4 mmol) and Boc2O (2.7 g, 12.3 mmol) were added and the mixture stirred at r.t. for 1.5 h. H2O was added and the product extracted with EtOAc.The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography (CH2Cl2/MeOH 99:1) affording 1.0 g (71%) of the title compound.1H NMR (CDCl3) delta 7.55 (d, 1H), 7.07 (dd, 1H), 6.70 (d, 1H), 4.76 (bs, 1H), 4.15 (d, 2H), 4.08 (bs, 2H), 1.46 (s, 9H).

The synthetic route of 4-Amino-3-iodobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIRATORIUS AB; US2012/40942; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 33348-34-4,Some common heterocyclic compound, 33348-34-4, name is 4-Amino-3-iodobenzonitrile, molecular formula is C7H5IN2, 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: A 25 mL Wattecs reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium O-ethyl dithiocarbonate 2 (1.8 mmol),CuCl (0.06 mmol), and DMF (2 mL). The reaction vessel was flushed with argon three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110C for 6 h.The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, and then HCl (3 mL, 3 mol/L) was added and stirred for another 30 min. The reaction mixture solution was extracted by ethyl acetate (3 ¡Á 20 mL). Subsequently, the combined organic solutions were dried by anhydrous sodium sulfate and the target product was purified by chromatography on a silica gel column (eluent: petroleum ether/ethyl acetate) togive the corresponding pure product 3. Complete characterization characterizationof the products (all known) is found in the Supplemental Materials (Figures S1-S13).

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

Reference:
Article; Liu, Lei; Zhu, Ning; Gao, Min; Zhao, Xiaole; Han, Limin; Hong, Hailong; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 5; (2016); p. 699 – 701;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 33348-34-4, A common heterocyclic compound, 33348-34-4, name is 4-Amino-3-iodobenzonitrile, molecular formula is C7H5IN2, 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: A 25 mL reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium o-ethyldithiocarbonate 2 (1.8 mmol), FeF3 (0.06 mmol), 2,2?-bis(diphenylphosphino)-1,1?-binaphthyl (0.03 mmol) and DMF (4 mL). The reaction vessel was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110 for 3 – 21 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, then 4 mL HCl (3mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by ethyl acetate (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous sodium sulfate and the target product was purified by silica gel colum chromatography (eluent: petroleum ether / ethylacetate) to give the corresponding pure product 3.

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; Gao, Min; Lou, Chunqing; Zhu, Ning; Qin, Weijing; Suo, Quanling; Han, Limin; Hong, Hailong; Synthetic Communications; vol. 45; 20; (2015); p. 2378 – 2385;,
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. 33348-34-4, name is 4-Amino-3-iodobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 33348-34-4

To a solution of 4-amino-3-iodobenzonitrile in THF (4 ml.) was added BH3.THF (1 M solution in THF 2.5 ml.) drop-wise. The reaction mixture was refluxed for 3 h and 2 N HCI (1.0 ml.) was added . The resulting mixture was refluxed for an additional 1 h and then concentrated in vacuo in order to afford the crude, which was re-crystallized in MeOH for characterization to give 150 mg (74 %) of yellow powder. 4-amino-3-iodobenzylammonium chloride. ^ NMR (250 MHz, DMF) d 8.90 (s, broad, 3H, +NH3), 7.88 (d, J = 2.0 Hz, 1H, CHar), 7.42 (dd, J = 8.3, 2.1 Hz, 1H, CHar), 6.93 (d, J = 8.3 Hz, 1H, CHar), 5.81 (s, 6H, HCI), 4.06 (q, J = 5.6 Hz, 2H, CH2). (0104) 13C NMR (63 MHz, DMF) d 151.64 (Car-+NH3), 149.11(Car), 140.44 (CHar), 131.17 (CHar), 124.75 (Car), 114.86 (CHar), 82.93(Car-I), 42.30 (CH2).

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; UNIVERSIDAD COMPLUTENSE DE MADRID; FUNDACION PARA LA INVESTIGACION BIOMEDICA DEL HOSPITAL INFANTIL UNIVERSITARIO NINO JESUS; FUNDACION PARA LA INVESTIGACION BIOMEDICA DEL HOSPITAL UNIVERSITARIO LA PRINCESA; VALLET REGI, Maria; BAEZA GARCIA, Alejandro; VILLAVERDE CANTIZANO, Gonzalo; CASTILLO ROMERO, Rafael; RAMIREZ ORELLANA, Manuel; MELEN FRAJLICH, Gustavo; GONZALEZ MURILLO, Africa; ALFRANCA GONZALEZ, Arantzazu; (49 pag.)WO2019/185586; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 33348-34-4, A common heterocyclic compound, 33348-34-4, name is 4-Amino-3-iodobenzonitrile, molecular formula is C7H5IN2, 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.

Description for D20; delta-Cyano-IH-indole^-carboxylic acid (D20); A suspension of 4-amino-3-iodobenzonitrile (2.44 g), 2-oxopropanoic acid (2.64 g), DABCO (3.36 g), and Pd(OAc)2 in DMF (30 ml.) was heated to 105 0C and stirred at that temperature for 1 hour. The solvent was evaporated. EtOAc (200 ml.) was added and the resulting solution was washed with water (100 ml.) and aqueous NaOH solution (20 ml_). The combined aqueous solution was extracted with EtOAc (3 x 150 ml_). The organic fractions were combined. The combined solution was dried over anhydrous magnesium sulfate. The dried solution was concentrated. The residue was triturated to afford 5-cyano-1 /-/-indole-2-carboxylic acid (D20) (1.1 g) as a brown solid.

The synthetic route of 33348-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/153307; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com