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22nd March 2012 @ 06:12
Repeat of MNR21-3 on the same scale. [url=http://onlinelibrary.wiley.com/doi/10.1002/chem.201002046/abstract;jsessionid=723FBA3B0C773C23E60CDC106E8C9FC1.d02t03?systemMessage=Wiley+Online+Library+will+be+disrupted+24+March+from+10-14+GMT+%2806-10+EDT%29+for+essential+maintenance]DOI: 10.1002/chem.201002046[/url] [b]Hazard and Risk Assessment:[/b] [data]3737[/data] Water (60 mL) was added to a 500 mL round-bottomed flask. Sodium hydroxide (60.0 g, 1.5 mol) was added portionwise followed by a mixture of 2-phenylethylamine (24.3 mL, 0.19 mol), chloroform (16.0 mL, 0.19 mol), and benzyltriethylammonium chloride (400 mg, 1.8 mmol) in dichloromethane (60 mL)dropwise over 10 mins. The reaction mixture was then refluxed for 4 hours. The reaction mixture was then allowed to cool to room temperature and was diluted with ice and water (50 mL), the organic layer was separated and retained, the aqueous layer was extracted with DCM (2 x 60 mL). The organic fractions were then combined and washed with HCl (1M) (3 x 100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude as a dark orange oil (23.90 g) The crude was passed through a short column (60-100 EtOAC) collecting the top running spot. After concentration, (2-isocyanoethyl)benzene (MNR21-4) was afforded as a dark yellow oil (17.618 g, 134.31 mmol, 70%) [b]Characterisation[/b] [data]4910[/data][data]4912[/data] 1H NMR (400 MHz, CDCl3): d = 7.37-7.21 (m, 5H), 3.60 (tt, J = 10.6, 1.9 Hz, 2H), 2.98 (tt, J = 10.6, 1.9 Hz, 2H) [data]188[/data] 13C NMR – MW34-1 (50 MHz, CDCl3): d = 156.6, 136.7, 128.7, 128.7, 127.2, 42.9 (t, J = 6.5) 35.6. [data]192[/data] Vmax/cm-1 2147, 1454 [blog]309[/blog] *lab book entry closed
Attached Files
mnr21-4_1H.pdf
mnr21-4_frac1.zip