Water → 3-Methoxy-10-methyl-11-phenyl dibenzo(b,f)thiepin

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Reaction Steps

7-hydroxy-11-[(2-carboxy)ethyl]-10-phenyldibenzo[b,f]thiepin (1.87 g) in dry dimethylformamide (25 ml) was treated with sodium hydride (0.4 g of 75%) and stirred, first at room temperature and then at 50° C. until effervescence ceased. A solution of 1-chloro-2-NN-dimethylamino-ethane in toluene (15 ml of 1 M) was added and the mixture was heated with stirring under argon to 100° C. After 1.5 hours the mixture was allowed to cool, treated with water and extracted three times with ethyl acetate. The ethyl acetate solution was evaporated and the residue dissolved in methanol (10 ml) and 10% aqueous sodium hydroxide (5 ml) and refluxed for 20 minutes. The solvent was mostly removed and the sodium salt was dissolved in 200 ml of boiling water. Carbon dioxide was passed through the boiling solution until the pH fell to 8. This was extracted three times into ethyl acetate with a little methanol. The solution was dried and evaporated.

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