Trifluoroacetylation and Subsequent Pyrolysis of 2-Amino-2-oxazolines
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概要
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Treatment of 2-amino-5-phenyl-2-oxazoline (I) with trifluoroacetic anhydride gave 1,3-bis (2,2,2-trifluoroacetyl)-1-[2-(2,2,2-trifluoroacetyloxy)-2-phenylethyl] urea (II). Compound II was pyrolyzed at 120℃ to give 2,2,2-trifluoroacetyl isocyanate (III) and 2,2,2-trifluoro-N-[2-(2,2,2-trifluoroacetyloxy)-2-phenylethyl] acetamide (IV). Compound II was readily hydrolyzed to give 1-(2,2,2-trifluoroacetyl)-3-[2-(2,2,2-trifluoroacetyloxy)-2-phenylethyl] urea (VI). Compound VI was pyrolyzed at 230℃ to give 2,2,2-trifluoroacetamide (VII) and 2,2,2-trifluoro-N-(E)-styrylacetamide (VIII). It was considered that the formation of VIII proceeded through the intermediate 2-(2,2,2-trifluoroacetyloxy)-2-phenylethyl isocyanate (XI) or 1-(2,2,2-trifluoroacetyl)-3-(E)-styrylurea (XII), as shown in Chart 1.
- 公益社団法人日本薬学会の論文
- 1982-09-25
著者
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山本 典子
Osaka College Of Pharmacy
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柴田 恵
Osaka College Of Pharmacy
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田中 千秋
Osaka College Of Pharmacy
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那須 啓子
Osaka College of Pharmacy
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