A new and convenient in-situ method of generating phenyl isocyanates from anilines using oxalyl chloride

Tetrahedron Letters

Volumn 45, Issue 24, 2004, Pages 4769-4771

  Oh, Lynette M ^a   Spoors, P Grant ^a   Goodman, Richard M ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

Anilines; Oxalyl chloride; Phenyl isocyanates

Indexed keywords

ANILINE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; OXALIC ACID DERIVATIVE;

ACYLATION; ARTICLE; DECOMPOSITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; THERMAL ANALYSIS;

EID: 2442663784     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.043     Document Type: Article

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34. HPLC samples were diluted with 50:50 methanol/acetonitrile to form the oxamic methyl ester, whose presence was confirmed by LCMS
35. To facilitate the carbamate formation of electron-rich isocyanates (entries 2 and 3, 5.0 g scale), the reactions were cooled down to 20°C and 65 mL of MeOH and sodium methoxide (0.5 mL; 25% wt % solution in methanol) were added