Sodium Hydroxide → HCID 14372824, compound

Participants

Reaction Steps

Tetrahydrothiopyran-4one (10.0 g) was mixed with anthranilonitrile (5.08 g) and the mixture warmed at 60° until a homogeneous solution was obtained. Freshly fused ZnCl2 (8.2 g) was then added portionwise and the temperature of the reaction mixture raised to 120°. After 2 hours it was cooled and distributed between 10% NaOH and 2-butanone. The organic phase was separated, dried, and concentrated and the crude product triturated with Et2O and then passed over a silica gel column (5% Et3N-ethyl acetate). The product-containing fractions were concentrated and the product recrystallized from toluene to give 3.66 g, mp 214°-216°.

Provenance & Evidence