Reaction #3045

Reaction equation

3,5-di-(2-propenyl)-4-hydroxybenzaldehyde

rhodanine

sodium acetate

→

5-[(3,5-di-2-propenyl-4-hydroxyphenyl)-methylene]-2-thioxo-4-thiazolidinone

Yield 94.6%

Solvents

acetic acid

Conditions

Procedure

3,5-di-(2-propenyl)-4-hydroxybenzaldehyde (50.5 g), 36.6 g of rhodanine and 164 g of sodium acetate were heated together at reflux temperature in 1.25 liter of acetic acid for 14.5 hours. The resultant solution was cooled, poured into 2 liter of ice water to yield, upon separation, about 75 g of 5-[(3,5-di-2-propenyl-4-hydroxyphenyl)-methylene]-2-thioxo-4-thiazolidinone, m.p. 157°-160° C.

Source