Iodine-catalyzed one-pot synthesis of amides from nitriles via Ritter reaction

Tetrahedron Letters

Volumn 51, Issue 21, 2010, Pages 2813-2819

  Theerthagiri, Palani ^a,b   Lalitha, Appaswami ^a   Arunachalam, Pirama Nayagam ^b  

^a PERIYAR UNIVERSITY   (India)

^b SYNGENE INTERNATIONAL LTD   (India)

Author keywords

Alcohols; Amides; Iodine catalyzed; Nitriles; Ritter reaction

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL; AMIDE; IODINE; NITRILE; NITROMETHANE; TETRAHYDROFURAN; TOLUENE; XYLENE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; HEATING; HIGH TEMPERATURE; ONE POT SYNTHESIS; RITTER REACTION;

EID: 77951093091     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.057     Document Type: Article

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33. General experimental procedure for synthesis of amides: A mixture of alcohol (1 mmol), nitrile (1.1 mmol), iodine (20 mol %), and water (2 equiv) was placed in a sealed tube and heated to 110 °C for the appropriate time as mentioned in Table 2. After completion of the reaction (monitored by TLC), saturated sodium thiosulfate in water was added and extracted with ethyl acetate. The organic layer was separated and washed with water and brine and dried over sodium sulfate, concentrated to furnish the desired amides. When necessary, the obtained amides were purified by crystallization using petroleum ether/ethyl acetate (8:2).
34. General experimental procedure for synthesis of tert-butyl amides: A mixture of tert-butyl acetate (2 equiv), nitrile (1 mmol), iodine (20 mol %), and water (2 equiv) were placed in a RB flask and heated to110 °C for the appropriate time as mentioned in Table 3. After completion of the reaction (monitored by TLC), saturated sodium thiosulfate in water was added and extracted with ethyl acetate, the organic layer was separated and washed with water and brine and dried over sodium sulfate and concentrated. The obtained tert-butyl amides were purified by flash chromatography.