2-Bromobenzoyl isothiocyanate → tert-Butyl 2-(3-(2-bromobenzoyl)thioureido)-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 2-amino-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.28 g, 1.00 mmol) and 2-bromobenzoyl isothiocyanate (0.24 g, 1.00 mmol) were dissolved in THF (5 mL) and heated at 50° C. for 22 hours. The solvent was removed and EtOH (10 mL) was added. The product was filtered and rinsed with EtOH (2×10 mL). tert-Butyl 2-(3-(2-bromobenzoyl)thioureido)-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.26 g, 0.49 mmol, 49% yield) was isolated as a white solid. 1H NMR (400 MHz, CDCl3) δ 14.64 (s, 1H), 9.04 (s, 1H), 7.75 (apparent dd, J=7.6, 1.8 Hz, 1H), 7.67 (apparent dd, J=7.9, 1.1 Hz, 1H), 7.45 (apparent td, J=7.5, 1.3 Hz, 1H), 7.40 (apparent td, J=7.7, 1.9 Hz, 1H), 4.74 (apparent t, J=1.5 Hz, 2H), 2.77 (t, J=1.5 Hz, 2H), 1.63 (s, 9H), 1.31 (s, 6H).

Provenance & Evidence