Category: 66389-80-8

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. 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H16N2O2

(2) To a solution of hydroxylamine hydrochloride (2.24 g, 32.3 mmol) in dimethyl sulfoxide (10.6 mL), triethylamine (4.51 mL, 32.4 mmol) was added and the resulting mixture was stirred at room temperature for an hour. The precipitating salt was filtered and washed with THF. The THF was distilled off under reduced pressure and after adding the foregoing compound (n-2) (1.50 g, 6.46 mmol), the resulting mixture was stirred at 75 C. for 15 hours. The reaction mixture was cooled to room temperature and after adding water, extraction was conducted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvents were distilled off under reduced pressure to give tert-butyl 4-(N?-hydroxycarbamimidoyl)benzylcarbamate (n-3) (amount, 1.70 g; yield, 99%).

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 66389-80-8.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; IKEGAMI, Satoru; WATANABE, Atsushi; HIRANO, Kimio; OHYAMA, Tadashi; (56 pag.)US2016/130232; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H16N2O2

General procedure: To a round-bottom flask equipped with a stir bar was added 28a-b (1.0 eq), hydroxylamine hydrochloride (2.0 eq), NaHCO3 (4.0 eq), and methanol (10 mL/mmol). The reaction was refluxed and stirred in a pre-heated 75 C. oil-bath for 6 h. After cooling to room temperature, the precipitate was filtered off and washed with methanol. The filtrate was concentrated in vacuo and further purified on a silica gel column. Example 89 Synthesis of 215 tert-Butyl (E)-(4-(N?-hydroxycarbamimidoyl)benzyl) carbamate (29a) (0246) The synthesis follows the general procedure described in Example 88. Yield: 65%. MP: 142-145 C. 1H NMR (400 MHz, DMSO-d6) delta 9.57 (s, 1H, -OH), 7.61 (d, J=8.1 Hz, 2H, -ArH), 7.40 (t, J=6.1 Hz, 1H, -NHCO-), 7.22 (d, J=8.1 Hz, 2H, -ArH), 5.77 (s, 2H, -NH2), 4.13 (d, J=6.1 Hz, 2H, -ArCH2-), 1.40 (s, 9H, -CH3).

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; Washington University; Tu, Zhude; Rosenberg, Adam; Liu, Hui; Han, Junbin; US2019/2450; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl 4-cyanobenzylcarbamate

130 g (0.56 mol) of product 3a, 58.4 g (0.84 mol) of hydroxylamine×HCl and 146 ml of DIEA were dissolved in 1.5 l of methanol. The mixture was boiled under reflux for 6 h and then stirred at room temperature overnight. The solvent was removed in vacuo, and the oily residue was dissolved in 1.5 l of acetic acid, mixed with 160 ml (1.68 mol) of acetic anhydride and stirred for 30 min. The solvent was removed in vacuo, and the residue was taken up with ethyl acetate and washed 3× with NaCl-saturated water and then dried over Na2SO4. The solvent was removed as far as possible in vacuo, and the product was crystallized from ethyl acetate. Yield: 110.6 g (0.36 mol) of crystalline solid, HPLC: 39.76% B

According to the analysis of related databases, 66389-80-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Stuerzebecher, Joerg; Steinmetzer, Torsten; Schweinitz, Andrea; Sturzebecher, Anne; Donnecke, Daniel; US2007/66539; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C13H16N2O2

(2) To a solution of hydroxylamine hydrochloride (2.24 g, 32.3 mmol) in dimethyl sulfoxide (10.6 mL), triethylamine (4.51 mL, 32.4 mmol) was added and the resulting mixture was stirred at room temperature for an hour. The precipitating salt was filtered and washed with THF. The THF was distilled off under reduced pressure and after adding the foregoing compound (n-2) (1.50 g, 6.46 mmol), the resulting mixture was stirred at 75 C. for 15 hours. The reaction mixture was cooled to room temperature and after adding water, extraction was conducted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvents were distilled off under reduced pressure to give tert-butyl 4-(N?-hydroxycarbamimidoyl)benzylcarbamate (n-3) (amount, 1.70 g; yield, 99%).

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 66389-80-8.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; IKEGAMI, Satoru; WATANABE, Atsushi; HIRANO, Kimio; OHYAMA, Tadashi; (56 pag.)US2016/130232; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 66389-80-8 as follows. category: nitriles-buliding-blocks

Synthesis of SiR-Tz (FIG. 8) (0148) 4-Cyanobenzylamine HCl was Boc-protected with Boc-anhydride. The Boc-protected amine was converted to the tetrazine 8 (Yang, et al., 2012, Angew. Chem., Int. Ed. 51:5222-5225). The Boc-group of tetrazine 8 was removed by treating the compound with a 1:1 mixture of TFA and dichloromethane and immediately coupled with SiR-OH (Lukinavicius, et al., 2013, Nature Chem. 5:132-139) mediated by TBTU and iPr2NEt.

According to the analysis of related databases, 66389-80-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yale University; ERDMANN, Roman; SHRADER, Alanna Schepartz; TOOMRE, Derek; (34 pag.)US2016/115180; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, belongs to nitriles-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 66389-80-8, HPLC of Formula: C13H16N2O2

tert- Butyl (4-cyanobenzyl)carbamate (1 g, 4mmol) was suspended in 10 mL ethanol and heated to 80C. To the solution was added 10 mL of aqueous hydroxylamine and the mixture was heated for 3 hours and allowed to cool to room temperature and stirred overnight. After concentration the residue was concentrated to half volume, and product extracted with ethyl acetate (3 x 15 ml). The combined organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness to yield white solid (890 mg) which was taken to the next step. Mass Spec, MH+ = 266

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

Reference:
Patent; TOSK, INC.; LENNEK, Annie L.; YANOFSKY, Stephen D.; FRENZEL, Brian D.; UNGASHE, Solomon B.; GARLAND, William A.; LIAW, Philip; (105 pag.)WO2020/33413; (2020); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, A new synthetic method of this compound is introduced below., Recommanded Product: 66389-80-8

c) N-Boc-4-aminomethyl-N-hydroxy-benzamidine; To a solution of N-Boc-4-aminoethylbenzonitrile (14g; 60mmol) in THF (500ml) is added at 50C a solution of hydroxy Ia mine in water (1/1 ; 80ml; 1.8 mol). The reaction mixture is then stirred at room temperature for 16 hours. The reaction mixture is diluted with water and THF is removed under vacuo. The resulting precipitate is collected by filtration and dried. Pure title compound is obtained by recrystallization from diethylether.

The synthetic route of 66389-80-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/37476; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, belongs to nitriles-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 66389-80-8, Product Details of 66389-80-8

Zn(OTf)2, 0.27g (2.5 mmol) of formamidine acetate, 58mg (0.25 mmol) nitrile ,0.20 mL DMF, and 0.40 mL (12.5 mmol) of anhydrous hydrazine was added. The vessel was sealed and the mixture was stirred in an oil bath at 30C for 36 hours. The reaction solution was cooled to room temperature and the seal was removed. Sodium nitrite (5.0 mmol, 345 mg) in 5 mL of water was slowly added to the solution and followed by slow addition of 1M HCl during which the solution turned bright red in color and gas evolved. Addition of 1M HCl continued until gas evolution ceased and the pH value is 3. (Caution: this step generates a large amount of toxic nitrogen oxide gasses and should be performed in a well ventilated fume hood). The mixture was extracted with EtOAc and the organic phase dried over sodium sulfate. The EtOAc was removed using rotary evaporation and the residue purified using silica column chromatography (Hexane:EtOAc=7: l) to give 50mg product as red solid, the yield is 70%. 1H NMR (500 MHz, CDC13) delta 1.49 (9H, s), 4.45 (2H, d, J = 5 Hz ), 4.97 (1H, bs), 7.53 (2H, d, J = 10 Hz), 8.60 (2H, d, J = 10 Hz), 10.21 (1H, s); 13C MR (125 MHz, CDC13) delta 39.07, 51.82, 118.84, 119.19, 120.76, 132.11, 141.12, 142.56, 149.36; HRMS [M+Na]+ m/z calcd. for [C9H16N502]+ 310.1276, found 310.1274.

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; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; DEVARAJ, Neal, K.; YANG, Jun; SECKUTE, Jolita; WO2013/152359; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, 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. Quality Control of tert-Butyl 4-cyanobenzylcarbamate

To a solution of hydroxylamine hydrochloride (2.24 g, 32.3 mmol) in dimethyl sulfoxide (10.6 mL), triethylamine (4.51 mL, 32.4 mmol) was added and the resulting mixture was stirred at room temperature for an hour. The precipitating salt was filtered and washed with THF. The THF was distilled off under reduced pressure and after adding the foregoing compound (n-2) (1.50 g, 6.46 mmol), the resulting mixture was stirred at 75C for 15 hours. The reaction mixture was cooled to room temperature and after adding water, extraction was conducted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvents were distilled off under reduced pressure to give tert-butyl 4-(N’-hydroxycarbamimidoyl)benzylcarbamate (n-3) (amount, 1.70 g; yield, 99%).

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

Reference:
Patent; Kaken Pharmaceutical Co Ltd; kegami, Satoru; Watanabe, Atsushi; Hirano, Kimio; Oyama, Tadashi; (62 pag.)KR2016/18745; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 66389-80-8 as follows. SDS of cas: 66389-80-8

To a round-bottom flask equipped with a stir bar was added 18a-b (1.0 eq), hydroxylamine hydrochloride (2.0 eq), NaHCO3 (4.0 eq), and methanol (10mL/mmol). The reaction was refluxed and stirred in a pre-heated 75C oil-bath for 6h. After cooling to room temperature, the precipitate was filtered off and washed with methanol. The filtrate was concentrated in vacuo and further purified on a silica gel column. 4.2.4.5 tert-Butyl (E)-(4-(N?-hydroxycarbamimidoyl)benzyl)carbamate (19a) Yield: 65%. MP: 142-145C. 1H NMR (400MHz, DMSO-d6) delta 9.57 (s, 1H, -OH), 7.61 (d, J=8.1Hz, 2H, -ArH), 7.40 (t, J=6.1Hz, 1H, -NHCO-), 7.22 (d, J=8.1Hz, 2H, -ArH), 5.77 (s, 2H, -NH2), 4.13 (d, J=6.1Hz, 2H, -ArCH2-), 1.40 (s, 9H, -CH3)

According to the analysis of related databases, 66389-80-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Luo, Zonghua; Rosenberg, Adam J.; Liu, Hui; Han, Junbin; Tu, Zhude; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 796 – 808;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts