Yield:-

Reaction Conditions:

with triethanolamine in ethanol;

Steps:

1.a (a)

(a) 2-Acetoxythioacetamide A stream of dry H₂ S gas was passed rapidly into a solution of 2-acetoxyacetonitrile (150 g; 1.52 mole) and triethanolamine (20 ml) in dry ethanol (500 ml) with vigorous stirring. The internal temperature rose to ca. 55° C. The gas flow was maintained for 3 hours whereupon G.L.C. indicated that the reaction was complete. Excess H₂ S gas was blown off with a stream of nitrogen and solvent EtOH evaporated to dryness. The remaining sticky crystalline mass was extracted with boiling ether, a small insoluble residue being discarded. The combined extracts were treated with decolourising charcoal, filtered and evaporated to approximately 400 ml volume. On cooling to 0° C. there was obtained some 170 g. of somewhat sticky 2-acetoxythiocetamide. This was used for the next stage without further characterisation.

References:

US4123529,1978,A