N-tert-Butyl-N-chlorocyanamide: A new reagent for the efficient preparation of gem-chloronitroso compounds

Tetrahedron Letters

Volumn 46, Issue 47, 2005, Pages 8121-8123

  Kumar, Vinod ^a   Kaushik, M P ^a  

^a Process Technology Development Division   (India)

Author keywords

gem Chloronitroso compounds; Ketoximes; N tert Butyl N chlorocyanamide

Indexed keywords

CARBON TETRACHLORIDE; CHLORINE DERIVATIVE; CYANAMIDE; NITROGEN DERIVATIVE;

ARTICLE; ROOM TEMPERATURE;

EID: 27144525494     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.131     Document Type: Article

References (14)

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14. Typical experimental procedure: To a stirred solution of oxime (5 mmol) in dry carbon tetrachloride (10 ml), at room temperature, was slowly added N-tert-butyl-N-chlorocyanamide (1.0 equiv) in dry carbon tetrachloride (5 ml). The reaction took place immediately on mixing, as monitored by TLC and confirmed by the appearance of a blue colour in the reaction mixture (in the case of aliphatic oximes). If the products were liquid, the solution was concentrated and kept in a refrigerator overnight. Compound 4 precipitated (mp 12-13°C) and was filtered off immediately. The filtrate was evaporated to give the crude product, which on distillation under vacuum, afforded the pure product. If the products were solid, purification was carried out by recrystallization using DCM/petroleum ether (40-60°C) in a 3:7 ratio.