Direct preparation of primary amides by reaction of carboxylic acids and ammonia in alcohols using DMT-MM

Chemistry Letters

Volumn 37, Issue 12, 2008, Pages 1191-1192

  Mizuhara, Tsukasa ^b   Hioki, Kazuhito ^b   Yamada, Megumi ^b   Sasaki, Hideaki ^b   Morisaki, Daiki ^a   Kunishima, Munetaka ^a,b  

^a KANAZAWA UNIVERSITY   (Japan)

^b KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67650432963     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2008.1190     Document Type: Article

References (26)

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18. Abbreviations used in this report are as follows: DIPEA: diisopro-pylethylamine, HOBt: 1-hydroxybenzotriazole, PyBOP: O-(benzotriazol-l-yl)tris(pyrrolidino)phosphonium hexafluorophos-phate, HBTU: O-(benzotriazol-1-yl)-1,1,3,3-tetramethyluromum hexafluorophosphate, EDCA: 4-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide hydroehloride, DCC: dicyclohexylcarbodiimide, HOTT: S-(1-oxide-2-pyridinyl)-1, 1,3,3-tetramethyluronium hexafiuorophosphate, TOTT: S-(1-oxide-2-pyridinyl)-1,1, 3,3-tetra-methyluronium tetrafluoroborate.
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25. 3N instead of DIPEA decreased the yield; see ref. 16.
26. 4. The crude product was purified by preparative TLC (AcOEt) to give the corresponding 3-phenylpropanamide (27.7 mg, 93%) as a colorless crystal.