Efficient Routes for the Synthesis of Dinaphthosulfide (BINOL Derivatives) and Dibenzosulfide Aza Podands Containing Ethanolamine

Abstract

Four new dinaphthosulfide and dibenzosulfide aza podands were synthesized. The synthesis of these podands was performed under three different reaction conditions: 1) diester, K ₂ CO ₃ , methanol, and RT; 2) diester, ethanolamine, and microwave (MW); and 3) diacid dichloride, ethanolamine, Et ₃ N, CH ₂ Cl ₂ , RT. Two kinds of diester (dinaphthosulfide and dibenzosulfide) were used for the preparation of dihydroxy podands. These dihydroxy podands were reacted with thionyl chloride to afford dichloro podands. The second route gave excellent yields of dihydroxy podands. Dichloro podands are more soluble than dihydroxy podands in conventional solvents such as methanol, chloroform, and acetonitrile.

Keywords:

• Aza podand
• 2-chloro ethanolamine
• dibenzosulfide
• dinaphthosulfide
• synthesis

Notes

^a Solubility measured at concentration of 0.05 g/mL.

^b Insoluble.

^c Soluble after heating.

^d Soluble in room temperature.