Sodium Iodide → HCID 19905868, compound

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: ##STR9##

1. additionA mixture containing
2. temperaturewas refluxed for two hours
3. filtrationThe reaction mixture was filtered
4. customthe filtrate evaporated
5. customto yield a yellow residue
6. temperaturerefluxed for one hour The resulting mixture
7. filtrationwas filtered
8. customthe filtrate evaporated to dryness
9. customto yield a red residue which
10. temperaturethe resulting mixture was refluxed for 1.5 hours
11. temperatureThe mixture was cooled
12. extractionextracted twice with 20 ml of chloroform
13. dry with materialThe combined extracts were dried over sodium sulfate
14. filtrationfiltered
15. customevaporated

ORD record

ord-30be5995bb0146959e2fb90a143020d1

Source dataset

uspto-grants-1992_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05097097