Methyl iodide → 3-methylthio-2H-1,4-benzothiazine

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Reaction Steps

In a one liter flask is placed 10.8 parts of prewashed sodium hydride in 150 parts of N,N-dimethyl-formamide (DMF) at room temperature. After stirring for five minutes under nitrogen atmosphere, 30 parts of 2H-1,4-benzothiazine-3(4H)-thione[J. Med. Chem., 12, 290(1969)] is added in portions over a period of 30 minutes and continuously stirred at room temperature for 20 minutes. To the reaction mixture is then added 15 parts of methyl iodide and the mixture stirred at room temperature for 20 minutes under nitrogen. Removal of solvent by vacuum distillation under nitrogen affords 3-methylthio-2H-1,4-benzothiazine as the residue. Since the product is subject to spontaneous hydrolytic decomposition, it is not usually isolated for the purposes of this invention but instead employed as the solution in DMF preparable via the foregoing procedure.

Provenance & Evidence