Methanol → 4,4'-Bicyclohexanediyl dianthranilate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4,4′-bicyclohexanol (49.5 grams, 0.25 mol; obtained from Sigma-Aldrich), isatoic anhydride (122 grams, 0.75 mol), and 1,4-diazabicyclo[2.2.2]octane (66.0 grams, 0.50 mol) in 200 milliliters of dimethyl formamide was stirred at 120° C. for 1 hour, then was cooled to about 80° C. The solution was then treated first with dimethyl formamide (100 milliliters) and then with methanol (900 milliliters). The resultant suspension was stirred for 2 hours, and then was filtered. The solid was washed with 4×100 milliliter portions of methanol and was dried at 60° C. for 20 hours. The 4,4′-bicyclohexanediyl dianthranilate product was obtained as a cream solid (58.2 grams, 53 percent yield) which was adjudged by 1H-NMR spectroscopy to be pure (greater than 98 percent). The melting point of this product as measured by Differential Scanning Calorimetry was 236° C.

Provenance & Evidence