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9th November 2011 @ 00:42
Repeat of MNR15-1:- Preparation of (R)-O,O'-1,1'-binaphthyl-2,2'-diyl bis(dimethylcarbamothioate) (MNR15-2)

MNR15-2%20scheme.png

mnr15-2.PNG

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

Procedure

To an ice cooled solution of (R)-1,1'-Bi(2-naphthol)(0.820 g, 2,86 mmol) in dry DMF (10 mL) under argon was added sodium hydride (60% oil dispersion) (0.29 g, 7.16 mmol). The reaction was allowed to warm to room temperature and stirred for 10 mins. N,N-dimethylthiocarbamoyl chloride (0.78 g, 6.30 mmol)was added 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) and allowed to stand over night (to try and get better precipitation) The solid was filtered and washed with water and dissolved in DCM, dried over magnsium sulfate, filtered and concentrated to give an oily gum - not like before.

Crude 0.744g

1H NMR - MNR15-2 crude - nowhere near as clean as mnr15-1

Needs further purification.

Column, 10-20% EtOAc/Hex

1H NMR - MNR15-2 frac 3-6 - product, not as clean as MNR15-1 crude!
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Attached Files
mnr15-2.PNG
MNR15-2 scheme.png
mnr15-2.pdf
mnr15-2_frac3-6.pdf