Supplier From
Hangzhou,
China
Supplier From
Hangzhou,
China
General method: Dissolve the mixture of cyclohexanone (1 mmol), propiononitrile (1 mmol), elemental sulfur (1 mmol), and BSA (20 mg) in 1 mL DMF. The reaction is carried out at 50C and 200 rpm. After the reaction is completed, remove BSA by filtration to terminate the reaction. For high yield products, pour the reaction mixture into water to allow the solid product to precipitate, then filter and dry. For low yield products, the crude product is purified by rapid column chromatography on silica gel, using a mixture of petroleum ether/ethyl acetate as the eluent. The structure of the product is confirmed by IR, 1H NMR and 13C NMR spectra. 1H NMR (400 MHz) and 13C NMR (100 MHz) spectra were recorded on a Bruker Avance 400 spectrometer, using CDCl3 as the solvent and TMS as the internal standard. The IR spectrum was obtained using a Nicolet Nexus 470 FT-IR spectrophotometer. HPLC analysis was performed using an Agilent 1100 series system, equipped with an Agilent TC-C18 column (for 3a, 3Chemicalbookc, 3e, 3g, 3i, 3k: methanol/water = 60/40, flow rate 1.0 mL/min, detection wavelength 220 nm; for 3b, 3d, 3f, 3h, 3j, 3l: methanol/water = 60/40, flow rate 1.0 mL/min, detection wavelength 229 nm). All solvents used for column chromatography were purified by distillation before use. 2.2.1.2-Amino-4,5,6,7-tetrahydrobenz[b]thiophene-3-methanone (3a) is a yellow solid with a melting point of 140-142C (literature value 144-146C). IR (KBr): 3447, 3329, 2198 cm-1. 1H NMR (400 MHz, CDCl3)´4.62 (broad peak, 2H), 2.53-2.46 (multiplet, 4H), 1.85-1.73 (multiplet, 4H). 13C NMR (100 MHz, CDCl3): 159.9, 132.4, 120.7, 115.5, 88.8, 24.5, 24.1, 23.4, 22.1.
