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.
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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