Practical and efficient synthesis of N-halo compounds

Tetrahedron Letters

Volumn 46, Issue 7, 2005, Pages 1099-1101

  Zhong, Yong Li ^a   Zhou, Hua ^a   Gauthier, Donald R ^a   Lee, Jaemoon ^a   Askin, David ^a   Dolling, Ulf H ^a   Volante, Ralph P ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Amide oxidation; Amine oxidation; N halogenation; Sodium hypohalite; tert Butyl hypohalite

Indexed keywords

ACETIC ACID; AMIDE; AMINE; CHEMICAL COMPOUND; N HALO COMPOUND; REAGENT; SODIUM HYPOHALITE; TERT BUTYL ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS;

EID: 12344259837     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.088     Document Type: Article

References (27)

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26. Typical procedure for the preparation of N-halo compounds: To a solution of amine or amide (5.0 mmol), tert-butanol (0.25-1 equiv) in MTBE was slowly added acetic acid (1-1.5 equiv) and sodium hypohalite (1-1.5 equiv) at -5 to 0°C at the same time. The resulting solution was aged at 0°C for 15 min to 2 h. The organic layer was separated, washed with water, and then brine. The organic solution was concentrated to give desired N-halo compound in 90-100% yield
27. 3) δ: 171.9, 135.8, 129.2 (2C), 128.6 (2C), 127.1, 68.4, 61.5, 37.9, 14.1