Water → 1-(3-nitro-4-chloro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

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Reaction Steps

To 4-chloro-3-nitrobenzenesulfonyl chloride (1.0 g, 3.9 mmol) in dry DCM (10 mL), was added 2,3,4,5-tetrahydro-1H-benzo[b]azepine (0.57 g, 3.9 mmol). Diisopropylethylamine (1.3 mL, 7.8 mmol) was added and the mixture was stirred at ambient temperature for 16 hrs. DCM (20 mL) and 30 mL of water were added. The DCM layer was separated, washed with brine (20 mL×2), dried over MgSO4 and evaporated to give 1-(3-nitro-4-chloro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine 4-1 as a yellow solid (1.3 g, 85% yield). MS: 367 (M+H)+; tR=2.98 min (method 1).

Provenance & Evidence