Category: 1535-73-5

1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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 95 mg (0.32 mMol) 6-(amino-pyrimidin-4-ylsulfanyl)-naphthalene-1 -carboxylic acid, 85 mg (0.48 mMol) 3-trifluoromethoxy-aniline, 446 mul (3.2 mMol) Et3N and 4 mg (0.03 mMol) DMAP in 3 ml DMF, 0.37 ml (0.63 mMol) propylphosphonic anhydride are added. After 3 h at rt, the reaction mixture is worked up as described for Ex. 58, yielding the title compound: m.p.: 197-199 ¡ãC; MS: [M+1]+= 457.

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/31265; (2007); A2;,
Ether – Wikipedia,
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1535-73-5, 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 1535-73-5 as follows.

To a solution of 4-[2-(propargylamino)-2-oxo-acetyl]-1,3,5-trimethyl-pyrrol- 2-carboxylic acid 6 (250 mg, 1.0 mmol), 3-(trifluoromethoxy)aniline (227 mg, 1.3 mmol) and DIPEA (330 muL, 2.0 mmol) in pyridine (10 mL) was added HATU (0.65 g, 1.8 mmol) at room temperature. The mixture was stirred at 65 ¡ãC for 18 h. The reaction mixture was then poured into a saturated solution of ammonium chloride and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (Hexanes:EtOAc = 6:4 v/v) to give compound 55 as a white powder (34percent, 135 mg, 0.3 mmol). 1H NMR (400 MHz, Acetone-d6) delta 9.57 (s, 1H), 8.18 (s, 1H), 8.02 (s, 1H), 7.81? 7.67 (m, 1H), 7.50 (t, J = 8.2 Hz, 1H), 7.16? 7.06 (m, 1H), 4.17 (dd, J = 5.8, 2.6 Hz, 2H), 3.71 (s, 3H), 2.75 (t, J = 2.5 Hz, 1H), 2.45 (s, 3H), 2.32 (s, 3H). MS (ESI): m/z [M+H]+ calcd for C20H19F3N3O4: 422.4, found: 422.4.

According to the analysis of related databases, 3-Trifluoromethoxyaniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EMORY UNIVERSITY; SCHINAZI, Raymond F.; BOUCLE, Sebastien; AMBLARD, Franck; SARI, Ozkan; BASSIT, Leda; (169 pag.)WO2017/156255; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1535-73-5, 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 1535-73-5 as follows.

General procedure: Two mmol 5b1?5b20 was added to a dichloromethane solution containing 0.3 mL triethylamine at 0 ¡ãC. Then 1.2 equiv. 3-chloropropionyl chloride was dissolved in dry dichloromethane, and the obtained mixture was slowly added to the aniline solution at 0 ¡ãC. The reaction mixture was allowed to slowly warm up to room temperature, extracted with dichloromethane and finally washed with 2 M HCl. The organic phase was combined and dried with anhydrous MgSO4. Filtration and removal of the solvent under reduced pressure gave the crude product. The desired product was further purified by flash column chromatography with petroleum ether-EtOAc (20:1 to 10:1) to produce 6b1?6b20.

According to the analysis of related databases, 3-Trifluoromethoxyaniline, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhu, Kongkai; Song, Jia-Li; Tao, Hong-Rui; Cheng, Zhi-Qiang; Jiang, Cheng-Shi; Zhang, Hua; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3693 – 3699;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1535-73-5, 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. 1535-73-5 name is 3-Trifluoromethoxyaniline, 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.

To a solution of 3-trifluoromethoxy aniline (0.5 g, 2.8 mmol) in CH2Cl2 (70 ml) is added dropwise, phenyl chloroformate (1.06 ml, 8.5 mmol) and pyridine (0.226 ml, 2.8 mmol) at 0 C. The reaction mixture is stirred at 0 C. for 30 min. The solution is washed with 0.1 N HCl, 5% NaHCO3, brine, and concentrated under vacuum. The resulting solid is crystallized from n-heptane to give white needles 0.6 g (71% yield). HRMS (EI) calcd for C14H10F3NO3 297.0613, found 297.0613. Example 405 (from 4-amino-3-methylphenol and phenyl 3-(trifluoromethoxy)phenylcarbamate) is prepared by following Method D, making non-critical modifications. The resulting residue is triturated with CH3CN to give an off white solid 0.07 g (33% yield). HRMS (ESI) calcd for C15H13N2O3F3+H 327.0956, found 327.0954.

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

Reference:
Patent; Piotrowski, David W.; Rogers, Bruce N.; McWhorter JR., William W.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Groppi JR., Vincent E.; Rudmann, Daniel G.; US2003/236287; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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 an ice-salt bathcooled solution of 3 (7.65 g, 50.0 mmol), hydrochloric acid (150 mL), a solution of sodium nitrite (3.6 g, 50.0mmol, 50 mL/H2O) was added dropwise, the mixture was left to stir for 30 minutes, followed by addition of 3-trifluromethoxyalinine dissolved in 50 mL alcohol, and neutralized with sodium acetate, the mixture was stirredfor 2 hours while the reaction temperature was kept between -5 to 0 ¡ãC, before pouring into 2000 mL cold waterand stirring, the solid was filtered and washed with water until the filtrate was colorless, the crude productobtained was recrystallized with ethyl acetate to give 8.55 g 4 as orange-yellow solid (50percent).

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

Reference:
Article; Fan, Yin-Bo; Li, Kun; Huang, Min; Cao, Yu; Li, Ying; Jin, Shu-Yu; Liu, Wen-Bing; Wen, Jia-Chen; Liu, Dan; Zhao, Lin-Xiang; Bioorganic and Medicinal Chemistry Letters; vol. 26; 4; (2016); p. 1224 – 1228;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem