Dichloromethane → 1,2,3,5,6,7-Hexahydro-4-isocyanato-s-indacene

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.77 g (0.01 mole) of 1,2,3,5,6,7-hexahydro-s-indacen-4-ylamine IX (Vejdelek et al. Coll. Czech Chem. Comm. 42: 3094 (1977) and 1.11 g (0.011 mole) of triethylamine in 25 mL of tetrahydrofuran was added 5.7 mL (0.011 mole) of a 1.93 M solution of phosgene in toluene. The reaction was stirred at room temperature for 15 min and at 70° C. for 15 min. The solvents were evaporated in vacuo. The residue was dissolved in hexane and purified on a plug of silica gel eluting with 10% CH2Cl2/hexane to give 1.79 g of non-labeled X (90%); mp 40-41° C. TLC:Hex/CH2Cl2::2/1 single-spot material Rƒ 0.70.1H-NMR (300 MHz CDCl3) δ: (2.13, t, 4H), (2.85, m, 8H), (6.93, s, 1H).

Provenance & Evidence