Category: 117832-17-4

Adding a certain compound to certain chemical reactions, such as: 117832-17-4, name is 2-Iodo-4,5-dimethylaniline, 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 117832-17-4, Application In Synthesis of 2-Iodo-4,5-dimethylaniline

60.8 g of lithium chloride is added to a solution of 15.5 g of [1,4]-benzoquinone in 350 ml of THF, and it is degassed with nitrogen. 3.2 g of palladium acetate and 23.7 g of benzyl acrylate are added and it is degassed with nitrogen for about 30 minutes. Than a solution of 35.1 g of 2-iodo-4,5-dimethylaniline (prepared according to J. Med. Chem. 2001, 44, 3856-3871) in 150 ml of THF is added and it is stirred overnight. It is filtered and the filtrate is evaporated. The solid residue thus obtained is triturated with ether. It is filtered, the filtrate is washed with a solution of NaOH 0.5N and then with water and with brine. It is evaporated and then the solid residue is purified by silica gel chromatography, eluting with a cyclohexane/EtOAc mixture (8/2; v/v). 57.6 g of the expected compound is obtained in the form of a white powder.1H NMR: DMSO-d6 (250 MHz): delta (ppm): 2.14 (3H, s); 2.19 (3H, s); 4.93 (1H, d); 5.18 (2H, s); 7.23 (1H, s); 7.30-7.45 (5H, m); 7.59 (1H, s); 7.72 (1H, dd); 10.05 (1H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-4,5-dimethylaniline, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI; US2012/277205; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 117832-17-4, 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 117832-17-4 as follows.

General experimental procedure: o-iodoaniline (1.0 mmol) and phenyl isothiocyanate (1.2 mmol) was mixtured and stirred for 1 h at room temperature (Method A), or o-iodoaniline (1.0 mmol) and phenyl isothiocyanate (1.2 equiv) was mixtured and stirred for 1 h at melting point temperature of phenyl isothiocyanate (Method B), or o-halobenzothioureas (1.0 mmol) (Method C), then anhydrous DMSO (5 ml) and base (3.0 mmol) was added, the stirring continued for about 5-10 h at 130 C (TLC monitor). After the reaction was completed, the reaction mixture was cooled to room temperature and ice-water was added, then the mixture was extracted with EtOAc. The combined organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and then the residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate (5:1 to 7:1)) on silica gel to provide the desired product.

According to the analysis of related databases, 117832-17-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Rui; Chen, Zhi; Yue, Liang; Pan, Wei; Zhao, Jun-Jie; Tetrahedron Letters; vol. 53; 34; (2012); p. 4529 – 4531;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 117832-17-4, 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. 117832-17-4 name is 2-Iodo-4,5-dimethylaniline, 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.

General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 muL, 0.5 mmol) 2a, (DMEDA) (3 muL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-4,5-dimethylaniline, and friends who are interested can also refer to it.

Reference:
Article; Yuan, Hua; Li, Kangning; Chen, Yongxin; Wang, Yu; Cui, Jiaojiao; Chen, Baohua; Synlett; vol. 24; 17; (2013); p. 2315 – 2319;,
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 117832-17-4 as follows. COA of Formula: C8H10IN

General procedure: To a two-necked round-bottomed flask fitted with a guard tube, PBr3 (2.7mmol, 0.26 mL), DMF (3 mmol, 0.23 mL) and chloroform (0.80 mL) were added, allowed to cool to 0 C and stirred for 0.5 h. After formation of colourless solid complex, 2-Iodo-4-methyl-phenylamine 2b (1 mmol) in chloroform (5 mL) was added and the reaction mixture was allowed to stir at r.t. for another 1-2 h. After completion, the reaction mixture was neutralized by adding saturated NaHCO3 solution and then extracted with DCM (3X 20 mL). Combined organic layer was washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was purified through column chromatography using silica gel (60-120 mesh) and petether/EtOAc (5:1) as eluent.

According to the analysis of related databases, 117832-17-4, the application of this compound in the production field has become more and more popular.

Some common heterocyclic compound, 117832-17-4, name is 2-Iodo-4,5-dimethylaniline, molecular formula is C8H10IN, 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. category: iodides-buliding-blocks

Preparation 2.65,6-Dimethyl-1 /-/-indole-3-carboxylic acid.(VIII): X = CH; R4 = Me; R5 = Me.Step 1 : 3-[(2-lodo-4,5-dimethylphenyl)amino]benzyl acrylate (XVIII).60.8 g of lithium chloride is added to a solution of 15.5 g of [1 ,4]- benzoquinone in 350 ml of THF, and it is degassed with nitrogen. 3.2 g of palladium acetate and 23.7 g of benzyl acrylate are added and it is degassed with nitrogen for about 30 minutes. Then a solution of 35.1 g of 2-iodo-4,5- dimethylaniline (prepared according to J. Med. Chem 2001 , 44, 3856-3871 ) in 150 ml of THF is added and it is stirred overnight. It is filtered and the filtrate is evaporated. The solid residue thus obtained is triturated with ether. It is filtered, the filtrate is washed with a solution of NaOH 0.5N and then with water and with brine. It is evaporated and then the solid residue is purified by silica gel chromatography, eluting with a cyclohexane/EtOAc mixture (8/2; v/v). 57.6 g of the expected compound is obtained in the form of a white powder.1H NMR: DMSO-de (250 MHz): delta (ppm): 2.14 (3H, s); 2.19 (3H, s); 4.93 (1 H, d); 5.18 (2H, s); 7.23 (1 H, s); 7.30-7.45 (5H, m); 7.59 (1 H, s); 7.72 (1 H, dd); 10.05 (1 H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 117832-17-4, its application will become more common.

Reference:
Patent; SANOFI; BADORC, Alain; BOLDRON, Christophe; DELESQUE, Nathalie; FOSSEY, Valerie; LASSALLE, Gilbert; YVON, Xavier; WO2012/146318; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

117832-17-4, Adding some certain compound to certain chemical reactions, such as: 117832-17-4, name is 2-Iodo-4,5-dimethylaniline, 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 117832-17-4.

General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 muL, 0.5 mmol) 2a, (DMEDA) (3 muL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

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 117832-17-4.

Reference:
Article; Yuan, Hua; Li, Kangning; Chen, Yongxin; Wang, Yu; Cui, Jiaojiao; Chen, Baohua; Synlett; vol. 24; 17; (2013); p. 2315 – 2319;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com