Electric Literature of 2734-70-5, The chemical industry reduces the impact on the environment during synthesis 2734-70-5, name is 2,6-Dimethoxyaniline, I believe this compound will play a more active role in future production and life.
A slurry of 398.1 (5.31 g, 28.7 mmol) and potassium hydroxide (3.06 g, 54.5 mmol) in water (20.5 mL) was heated at reflux for 1.25 h. The reaction was allowed to cool to RT and then 3 N HCl was added until the pH was 2. The mixture was extracted with EtOAc (4X). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to afford 398.2 (3.76 g, 83percent yield) as a light yellow oil. Note that 398.2 contains 35percent of the corresponding decarboxylation byproduct 4-ethylthiazole. Yhis mixture was used in the subsequent step. An ice-cooled solution of 398.2 (3.70 g, 65percent pure, 15.3 mmol) in DMF (55 mL) was treated with TEA (5.95 mL, 42.8 mmol) followed by HATU (7.0 g, 18.4 mmol) directly. After 5 min, 2,6-dimethoxyaniline (Amfinecom Inc., 2.3 g, 15.3 mmol) was added. The resulting brown solution was warmed to RT and stirred for 1.75 h. The reaction was then partitioned between water (275 mL) and EtOAc (2X). The combined organic layers were washed with water (1X) and brine (1X), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gelchromatography (eluent: 10-100percent EtOAc in hexanes) to provide Example 398.3 (2.54 g, 57percent yield) as a light yellow solid. LCMS-ESI (pos.) m/z: 293.0 (M+H)+.
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, 2,6-Dimethoxyaniline, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem