Synthesis and characterization of 2-hydroxy-N-methyl-N-phenyl-acetamide

来源期刊：中南大学学报(英文版)2002年第1期

论文作者：周忠诚 舒万艮

文章页码：25 - 29

Key words：-N-methyl-N-phenyl-acetamide; synthesis; acetylation; esterfication; ester interchange; char-acterization

Abstract: 2-hydroxy-N-methyl-N-phenyl-acetamide was synthesized by using N-methylaniline, chloracetyl chloride, anhydrous sodium acetate and methanol through the acetylation, esterfication and ester interchange steps. The acetylation of N-methylaniline with chloracetyl chloride, catalyzed by triethylamide with mole ratio n(C₆H₅NHCH₃)∶n(ClCH₂C(O)Cl)∶n(N(C₂H₅)₃)=1∶1.05∶1, the yield of 2-chloro-N-methyl-N-phenyl-acetamide(Ⅰ) was 93.8%; Then the esterification ofⅠwith anhydrous sodium acetate in the presence of phase transfer catalyst tetrabutyl ammonia bromide gave 97.3% yield of 2-acetoxyl-N-methyl-N-phenyl-ac-etamide (Ⅱ); The ester interchange of with methanol catalyzed by potassium hydroxide gave 2-hydroxy-N-methyl-N-phenyl-acetamide (Ⅲ) in 96.4% yield. And the total yield was 88.0%. IR and MS spectroscopy of products were analyzed and their characteristic peaks were assigned. Combining the results of elemental analysis, the molecular structure ofⅠ,ⅡandⅢwas identified.