A novel one-pot synthesis of hydroximoyl chlorides and 2-isoxazolines using N-tert-butyl-N-chlorocyanamide

Tetrahedron Letters

Volumn 47, Issue 9, 2006, Pages 1457-1460

  Kumar, Vinod ^a   Kaushik, M P ^a  

^a Process Technology Development Division   (India)

Author keywords

2 Isoxazolines; Aldoximes; Dipolarophiles; Hydroximoyl chlorides; N Phenylmaleimide; N tert Butyl N chlorocyanamide

Indexed keywords

2 ISOXAZOLINE DERIVATIVE; ALDOXIME; CYANAMIDE; HYDROXIMOYL CHLORIDE; N TERT BUTYL N CHLOROCYANAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; HALOGENATION; SYNTHESIS;

EID: 31444436379     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.083     Document Type: Article

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32. -1. The positive chlorine of N-tert-butyl-N-chlorocyanamide was determined by standard iodometric titration and found to be 26.54% (theoretical value 26.76%).
33. 4. Evaporation of the solvent gave a mixture of hydroximoyl chloride and tert-butylcyanamide. The pure hydroximoyl chloride was obtained either by recrystallization in DCM/petroleum ether (40-60°C) in a 3:7 ratio (in the case of solid products) or distillation under vacuum (in the case of liquid products).
34. 4. Evaporation of the solvent gave crude 2-isoxazolines, which were purified either by crystallization in DCM/petroleum ether (40-60°C) in a 3:7 ratio (in the case of solid products) or distillation under vacuum (in the case of liquid products).
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