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27th October 2011 @ 01:28
Step 1 of 3 towards (R)-1,1'-binaphthyl-2,2'-disulfonic acid as for MW45-1

MNR15-1%20scheme.png

MNR15-1%20table.PNG

Hazard and Risk Assessment:
HIRAC MNR15

Procedure

To an ice cooled solution of (R)-(+)-1,1'-Bi(2-naphthol)(0.50 g, 1.75 mmol) in dry DMF (5 mL) under argon was added sodium hydride (60% oil dispersion) (0.17 mg, 4.37 mmol). The reaction was allowed to warm to room temperature and stirred for 10 mins. The resulting yellow solid was gently heated to obtain a yellow dispersion to which N,N-dimethylthiocarbamoyl chloride (470 mg, 3.84 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 (15 mL). The pale brown solid was filtered off, washed with water and dissolved in DCM. The organic layer was separated from the remaining water, washed with brine and dried over sodium sulfate. After evaporation of the solvent a pale yellow, fine crystals was obtained.

682 mg,

1H NMR MNR15-1 first filter - clean product

More solid precipitated out of the aqueous layer after standing for one day and was filtered and washed with water.

39 mg,

1H NMR MNR15-1 second filter - some product, not clean
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Attached Files
HIRAC MNR15.pdf
MNR15-1 table.PNG
MNR15-1 scheme.png
mnr15-1_2nd filter.pdf