3-Hydroxy-N,N-dimethyl-2-butenethioamide

The title compound, C₆H₁₁NOS, is a 3-oxothioketone. It adopts an enol constitution which is stabilized by an intramolecular O—H...S hydrogen bond [O...S 2.895 (4) Å], even though some molecular orbital calculations suggested that the corresponding enethiol tautomer was most stable for 3-oxothioketone molecules. A Cambridge Structural Database search for the 3-oxothioketone skeleton found four enol structures but no enethiol ones. The mol­ecule lies on the crystallographic mirror plane.

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