Hydrazine hydrate (1:1) → 2,4-dibenzyloxy-5-isopropyl-N-(1-methyl-1H-indol-5-yl)-thiobenzamide

Participants

Reaction Conditions

Reaction Steps

Benzamide (A) was treated with Lawesson's reagent (3.46 g, 8.58 mmol, 0.6 equiv.) in 80 mL toluene at 110° C. for three hours. The reaction mixture was cooled to 0° C., and treated with hydrazine hydrate (1.50 g, 30 mmol) at 0° C. for 10 minutes to decompose by-product and excess reagent. Normal EtOAc/water workup, followed by recrystallization in EtOAc/hexane yielded 2,4-dibenzyloxy-5-isopropyl-N-(1-methyl-1H-indol-5-yl)-thiobenzamide (B) as yellow solid (6.20 g, 12 mmol, 83%).

Provenance & Evidence