Chlorotrimethylsilane → HCID 19904373, compound

5-Methyl-1,3,5-dithiazine, 2.7 g, was dissolved in 20 ml of tetrahydrofuran and 14 ml of 1.6 mole hexane solution of n-butyl lithium was dropwise added to the solution in an argon flow at -73° C. The mixture was stirred at the same temperature for an hour. Then, 2.4 g of trimethylsilyl chloride was dropwise added to the mixture at the same temperature. After completion of the dropwise addition, the temperature of the reaction mixture was gradually elevated to 0° C. and then stirred for 90 minutes to give crude 2-trimethylsilyl-5-methyl-1,3,5-dithiazine. Without purifying the crude product, 14 ml of 1.6 mole hexane solution of n-butyl lithium was dropwise added thereto at -10° C. followed by stirring for 30 minutes. After cooling to -73° C., a solution of 4.5 g of 4-phenoxypropiophenone in 10 ml of tetrahydrofuran was dropwise added. After completion of the dropwise addition, the temperature was gradually elevated to room temperature followed by stirring for 14 hours. After saturated sodium chloride aqueous solution was added to the mixture, it was extracted with chloroform. After drying the chloroform phase over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform : hexane =2 : 1) to give 5.5 g of the product.

1. additionAfter completion of the dropwise addition
2. customwas gradually elevated to 0° C.
3. stirringstirred for 90 minutes

ORD record

ord-eeb4ea704dbe48d6a291119cb62699a8

Source dataset

uspto-grants-1992_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05098928