N-methyl-2-phenoxyacetamide → HCID 21041753, compound

Participants

Reaction Steps

t-BuOK (0.55 mL of 1.0 N solution) in THF is added to a solution of phenoxy-N-methylacetamide (83 mg, 0.5 mmol) in THF (5 mL). After 5 minutes, butyl-4-isothiocyanatobenzoate (118 mg, 0.5 mmol) is added in one portion and the resultant mixture is stirred overnight. The crude mixture is filtered through a silica pad. After purification on silica eluting with 25% EtOAc in hexane, the desired acylthiouraea is obtained as a yellow oil (20 mg). 1H NMR (300 MHz, CDCl3): δ 12.38 (s, 1H), 9.44 (s, 1H), 8.10 (d, 2H, J=8.7 Hz), 7.86 (d, 2H, J=6.9 Hz), 7.42-7.35 (m, 2H), 7.11 (t, 1H, J=7.4 Hz), 7.02-6.98 (m, 2H), 4.64 (s, 2H), 4.34 (t, 2H, J=6.6 Hz), 1.81-1.72 (m, 2H), 1.55-1.43 (m, 2H), 0.99 (t, 3H, J=7.3 Hz). MS (APCI) m/z 387 [M+H]+.

Provenance & Evidence