Triethylamine → HCID 19804448, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-thiopheneacetic acid (2.00 g, 14.1 mmol) in benzene (70 mL) was added triethylamine (1.424 g, 14.1 mmol) followed by diphenylphosphoryl azide (3.868 g, 14.1 mmol) and the mixture was heated at 90° C. for 1 hour. Then N-methylhydroxylamine hydrochloride (2.36 g, 28.2 mmol) was added as a solution in water (1 mL) containing triethylamine (2.85 g, 28.2 mmol) and the mixture was heated at 90° C. for 18 hours. The reaction was then poured into aqueous saturated NH4Cl (70 mL) and extracted with ethylacetate (3×70 mL). The combined organic extract was dried over MgSO4 and concentrated. The resulting residue was purified by column chromatography (silica gel, ether-hexanes, 1:1) followed by crystallization in ethylaCetate-hexanes and gave the desired product (467 mg).

Provenance & Evidence