Electric Literature of 7160-22-7,Some common heterocyclic compound, 7160-22-7, name is N-(3,4-Dichlorophenyl)pivalamide, molecular formula is C11H13Cl2NO, 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.
N-(3,4-dichlorophenyl)-2,2-dimethylpropanamide (121 g) was dissolved in 720 mL THF and the solution was cooled to -50 0C. Butyllithium (433 mL, 2.5N in hex) was added while keeping the internal temperature between -45 0C and -35 0C. (final temp.: -35 0C) and held at -25 0C for 40 min. An hplc check of the reaction mixture revealed that 5-10 % of the starting material remained. An additional 25 mL of butyllithium was added at -30 0C and the reaction was at -30 to – 25 0C for a further 30 min (HPLC: no significant change). The reaction mixture was cooled to -45 0C and SO2 was bubbled though the solution until saturation appeared to have been reached. Subsequently, the reaction mixture was at – 10 to 0 0C for 45 min. Argon (2 double -balloon volumes) was bubbled through the solution following which the reaction mixture was cooled to -5 0C. Sulfuryl chloride (58.8 mL) was added while keeping the temperature below 22 0C. The reaction mixture was kept at 10-15 0C for 1 h (HPLC: complete). EtOAc was added and the mixture was concentrated, washed with water, saturated aqueous sodium bicarbonate and brine, dried over MgStheta4 and the solvent was evaporated in vacuo. The crude material crystallized and was triturated with hot hexane. Yield: 87.2 g 1H-NMR (DMSOd6) delta 7.60(d, J= 8.4Hz, IH), 7.34(d, J= 8.4Hz, IH), 1.43(9H, s).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(3,4-Dichlorophenyl)pivalamide, its application will become more common.
Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/124423; (2007); A2;,
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