Formamide → 3-Amino-2,2,4,4-tetramethylthietane

Participants

Reaction Conditions

Reaction Steps

Formamide (8.0 g, 178 mmol), 2,2,4,4-tetramethyl-3-oxothietane (1.0 g, 6.933 mmol) and aluminum chloride hexahydrate (100 mg) were placed in a Teflon lined Parr bomb and heated at 170° C. for 18 hours. The reaction was then cooled and taken up in water (20 ml). The aqueous solution was extracted with methylene chloride (3×20 ml), the extracts combined and concentrated under reduced pressure. The residue was refluxed with 1N HCl (20 ml) for 4 hours, the reaction cooled and washed with methylene chloride (2×20 ml). It was then brought to pH 14 by addition of 6N sodium hydroxide and extracted with the methylene chloride (3×20 ml). The combined extracts were dried (Na2SO4) and concentrated to give 0.600 g (60%) of title product, verified by its 1H-NMR spectrum.

Provenance & Evidence