Sodium Iodide → HCID 19905868, compound

Participants

Reaction Steps

A mixture containing desethyl-N-acetyl procainamide (1.25 g) (prepared as in Example VII and 0.8 g of chloroacetyl chloride dissolved in 25 ml of acetone was refluxed for two hours. The reaction mixture was filtered and the filtrate evaporated to yield a yellow residue. The yellow residue and 0.75 g of sodium iodide were dissolved in 20 ml of acetone and refluxed for one hour. The resulting mixture was filtered and the filtrate evaporated to dryness to yield a red residue which was then dissolved in 20 ml of methanol. To the methanol solution was added 20 ml of concentrated ammonium hydroxide and the resulting mixture was refluxed for 1.5 hours. The mixture was cooled and then extracted twice with 20 ml of chloroform. The combined extracts were dried over sodium sulfate, filtered and evaporated to yield N-p-acetamidobenzoyl-N'-ethyl-N'-aminoacetylethylene diamine. To 10 mg of N-p-acetamidobenzoyl-N'-ethyl-N'-aminoacetylethylene diamine was added 10 mg of 5-[(4,6-dichlorotriazin-2-yl)-amino]fluorescein dissolved in 1 ml of methanol and the reaction was allowed to proceed for ten minutes until a crude product had formed. The crude product was purified using silica gel thin-layer chromatographic techniques employing a developing solvent comprising a 1:1 mixture of chloroform:acetone to yield an N-P-acetamidobenzoyl-N'-ethyl-N'-aminoacetylethylene diamine-DTAF conjugate of the formula: ##STR10##

Provenance & Evidence