Z. Shu
2001
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Journal
Fine chemicals
Abstract
N Aryl N isopropyl 2 hydroxyacetamides are a series of important intermediates of useful pesticides.Four N aryl N isopropyl 2 hydroxyacetamides were prepared from four arylamines with different structure through N alkylation, N chloroacetylation,esterification and transesterification.Thus,keeping temperature at 10-20 ℃,potassium borohydride was added in parts to the solution of 4 trifluoromethylaniline and acetone in glacial acetic acid.It was then stirred at 20 ℃ for two hours to get N isopropyl 4 trifluoromethylaniline,in 86% yield.Chloroacetyl chloride was added dropwise at 40 ℃ to the solution of N isopropyl 4 trifluoromethylaniline in toluene and the temperature was raised to 75 ℃.The reaction lasted for two hours at this temperature with nitrogen bubbling through the solution. N (4 Trifluoromethylphenyl) N isopropyl 2 choloroacetamide was obtained in 92.9% yield. N (4 Trifluoromethylphenyl) N isopropyl 2 hydroxyacetamide was obtained by refluxing the mixture of N (4 trifluoromethylphenyl) N isopropyl 2 chroloroacetamide,methanol,triethylamide,potassium acetate and potassium carbonate in 88.2% yield.The overall yield was 70.5%.The product was identified by 1 HNMR and CIMS.