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5th December 2011 @ 02:50
After column chromatography, MNR21-1 does not look clean and has what looks like intermediate N-phenethylformamide present. Is it possible to drive this to pure MNR21 with addition of more POCL3?

MNR21-2%20scheme.png

Hazard and Risk Assessment:
HIRAC-MNR21

Procedure
MNR21-1 (0.380 g, <2.56 ) and triethylamine (1.07 mL, 7.67 mmol) (was dissolved in dry DCM (5 mL) and phosphoryl chloride (0.25 mL, 2.56 mmol) was added dropwise added at 0°C. The mixture was then stirred for 1 h at 0°C and a further 4 h at room temperature. The mixture was quenched with water and neutralized with NaHCO3 solution. The organic layer was separated and the aqueous solution was extracted DCM (x3). The organic layers were combined, dried over magnesium sulphate, filtered and evaporated afforded a dark brown oil.

Crude NMR showed very little change from starting material. Reaction not taken forward. Alternative route attempted, see KAB4-1

Preparation of (2-isocyanoethyl)benzene (KAB4-1)

Lab book page complete, MNR
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Attached Files
MNR21-2 scheme.cdx
MNR21-2 scheme.png
mnr21-2_crude.pdf