We have developed large-scale efficient procedures for the conversion of commercially available [(13) C]- or [(2) H3 ,(13) C]methanol and (13) CO2 or (13) C-labeled bromoacetic acid to 2-(phenylthio)[1,2-(13) C2 ]-, [1-(13) C]-, and [2-(13) C]acetic acid. The resulting derivatives are versatile, chemically stable, and nonvolatile two-carbon labeling precursors. We have used the (13) C-isotopomers of 2-(phenylthio)acetic acid in the synthesis of (13) C-labeled acrylic acid, methacrylic acid, and trans-crotonic acid.
The title compound, C10H11NO2S, was crystallized from solution as a by‐product during the synthesis of ethyl dimethyl oxamate. It should be noted that Nair & Sheeba [J. Org. Chem. (1999). 64, 6898–6900] also synthesized an oxamate as a by‐product during the transformation of acetoacetamides to cyclic compounds that was modified later to the synthesis of oxamates as primary products. NMR analysis of the compound did not provide a good basis for structural elucidation as it gave no indication of the presence of any heteroatom directly attached to the phenyl ring. X‐ray single‐crystal analysis revealed the direct attachment of an S atom to the ipso‐carbon of the phenyl ring. The resultant structure is a thiooxamate. The two carbonyl groups are not coplanar.
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