Water → methyl 3-isothiocyanatothiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Thiophosgene (1.1 ml, 1.1 eq) is added dropwise to a solution cooled down to 0° C. of 3-amino-2-thiophenecarboxylate (2 g, 1 eq) and triethylamine (3.9 g, 3 eq) in tetrahydrofuran (100 ml). The mixture is stirred for 15 min at 0° C. then water (70 ml) and diethyl ether (150 ml) are added. After decantation and extractions, the organic phases are combined, washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent:heptane 100% to heptane/ethyl acetate 7:3) produces the expected compound in the form of a beige powder (2.15 g, 85% yield).

Provenance & Evidence