Toluene → 4-chloro-N-ethylbenzothiazolone

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Reaction Steps

4-Chlorobenzothiazolone (4.64 g, 0.025 mole) was dissolved in a solution of sodium hydroxide (1.60 g, 0.0375 mole) in water (100 c.c.), and tetra-n-butylammonium bromide (0.24 g, 7.5×10-4 mole) and toluene (40 c.c.) were added thereto. Diethyl sulfate (5.78 g, 0.0375 mole) was added dropwise thereto at room temperature, and the mixture was stirred at room temperature for 1 hour, followed by phase-separation. The toluene layer was washed once with water, and the solvent was removed under reduced pressure to obtain 5.24 g of 4-chloro-N-ethylbenzothiazolone as white crystals. Yield 98.1%, purity 98.5%, m.p. 96°-98.5° C.

Provenance & Evidence