Lawesson's reagent → Benzyl N-(2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl)carbamate

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Reaction Steps

Add Lawesson's Reagent (6.52 g, 16.11 mmol) to a solution of benzyl N-[(3R)-2-oxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate (10.0 g, 32.22 mmol) in toluene (120 mL) and heat the reaction under nitrogen at 100° C. for 2.5 hours. Allow the reaction to cool and collect the precipitate by filtration. Wash (ether) the cake and dry it in a vacuum oven to give the title compound (5.5 g, 16.8 mmol). Concentrate the filtrate under reduced pressure and purify it by flash chromatography (30% hexane/CH2Cl2 to 100% CH2Cl2) to give the title compound (3.48 g, 10.7 mmol). The compound is partially racemized. The total yield of the title compound is 85%: MS (m/z): 327 (M+1).

Provenance & Evidence