2-Naphthalenecarboxamide, N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy- → 2-Naphthalenecarboxamide, N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy-4-[(1-phenyl-1H-tetrazol-5-yl)thio]-

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Reaction Steps

To a solution of 47.6 g of 1-hydroxy-N-[4-(2,4-di-t-amylphenoxy)-butyl]-2-naphthamide in 500 ml of carbon tetrachloride, was added a solution of 21 g of 1-phenyl-5-tetrazolylsulfur chloride (prepared according to Org. Synth. Coll., vol. II, page 445) in 200 ml of carbon tetrachloride. The mixture was refluxed overnight and concentrated in vacuo. The solid was recrystallized from 500 ml of acetonitrile, yielding 50 g of 1-hydroxy-4-(1-phenyl-5-tetrazolylthio)-N-[4-(2,4-di-t-amylphenoxy)-butyl]-2-naphthamide of formula ##STR10## which melted at 147°-148° C. (Synthesis as described in U.S. Pat. No. 3,701,783).

Provenance & Evidence