[CH2:1](O)C.C[O-].[Na+].[N:7]1[CH:8]=[CH:9][N:10]2[C:16]=1[CH2:15][C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[NH:12][C:11]2=[S:21].CI>O>[CH3:1][S:21][C:11]1[N:10]2[CH:9]=[CH:8][N:7]=[C:16]2[CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[N:12]=1Absolute ethanol (20,000 ml) is charged into a 20 gallon flask and stirred under nitrogen atmosphere; 517.62 g (9.58 moles) of sodium methoxide are added. After stirring for 30 minutes there is complete solution and 2,063 g (9.58 moles) of 11H-imidazo[1,2-c][1,3]benzodiazepine-5(6H)-thione are added. There is complete solution after stirring at room temperature for 1 hour. The solution is then cooled to 1°, and 1,360 g (9.58 moles) of methyl iodide are added over 30 minutes. The reaction mixture is stirred at 5° for 4 hours and at ambient temperature overnight. The turbid solution is then cooled to 5° and diluted with 50,000 ml of water. The resulting suspension is stirred for 4 hours at 5°. The solid is collected, and dried (5 mm Hg/60°) to give 5-methylthio-11H-imidazo[1,2-c][1,3]benzodiazepine, m.p. 87°-8°.
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