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2nd November 2011 @ 06:04
Preparation of rac-derivative of MNR15/16 as transformation to MNR17/18 failed to yield any product. rac-SM cheaper to work with and sort out problems.

MNR19-1%20scheme.png

MNR19-1%20table.PNG

Hazard and Risk Assessment:
As for MNR15:- HIRAC MNR15

Procedure

To an ice cooled solution of (rac)-1,1'-Bi(2-naphthol)(1.0 g, 3.49 mmol) in dry DMF (10 mL) under argon was added sodium hydride (60% oil dispersion) (0.35 g, 8.37 mmol). The reaction was allowed to warm to room temperature and stirred for 10 mins. Additional DMF (5 mL) was added to the mixture as it had gone completely solid then added to this dispersion was N,N-dimethylthiocarbamoyl chloride (0.95 g, 7.68 mmol) at room temperature and the resulting mixture was heated to 85°C for 1.5 h.

The yellow-brown mixture was cooled to room temperature and poured into 1% aqueous KOH solution (30 mL) where a off white solid precipitated out instantly. The solid was filtered and washed with water and dissolved in DCM, dried over magnsium sulfate, filtered and concentrated to give a light fluffy foam that slowly crystallised.

MNR19-1 crude - clean enough with traces of DMF

Future Work
Used in MNR20-1 - MNR20-6 and MNR20-7 - MNR20-8
Attached Files
MNR19-1 table.PNG
MNR19-1 scheme.png
mnr19-1_crude.pdf