Hydrochloric Acid → 3-Benzoyl-1-methyl-2-indolinethione

Participants

Reaction Conditions

Reaction Steps

A solution of 1-methyl-2-indolinethione (0.50 g, 3.06 mmol) in dry THF (3 mL) was added dropwise at 20° C. under N2 to a stirred suspension of NaH (0.13 g of a 60% w/w suspension in mineral oil, 3.37 mmol) in THF (2 mL). After gas evolution had ceased (5 minutes), a solution of the above phenacyl azide in THF (2 mL) was added dropwise, and the mixture was stirred at 20° C. for 1 hour, then poured into 6N HCl and extracted with EtOAc. The residue from the organic layer was chromatographed on silica gel. Elution with CH2Cl2 /petroleum ether (3:7) gave foreruns, and elution with CHlCl2 /petroleum ether (2:3) gave 3-benzoyl-1-methyl-2-indolinethione [XV: R1 =H, R3 =Me, R5 =C6H5] (24) (0.31 g, 38%); mp (trituration from MeOH) 132°-134° C.

Provenance & Evidence