Hydrochloric Acid → 8-chlorodibenzo[b,f][1,4]thiazepin-11(10H)-one

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Reaction Steps

A mixture of 2-(2-amino-4-chlorophenylsulfanyl)-benzoic acid methyl ester (189JO11) (149 mg, 0.51 mmol) and AlMe3 (355 μL, 0.71 mmol, 2 M in toluene) in CH2Cl2 (3 mL) was stirred at ambient temperature for six days, and then water was added carefully. The mixture was diluted with CH2Cl2, and was acidified with 2 M aqueous HCl. The organic phase was separated, dried (Na2SO4), concentrated and flash chromatographed (heptane:EtOAc, 5:1-3:1) to give 38 mg (29%) of the title compound (189JO13). MS (ESI) 262 (MH+).

Provenance & Evidence