Phosphorus pentachloride → HCID 86617337, compound

N-phenoxy-3-(phenylthio)acrylamide (0.50 g) was suspended to toluene (5 ml), then phosphorus pentachloride (0.42 g) was added thereto under ice-cooling and stirred at same temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved to ethanol (15 ml). Sodium salt of thiophenol (0.73 g) was added to the solution under ice-cooling and heat refluxing for 2.5 hours. t-Butyl methyl ether (100 ml) was added to the reaction mixture, washed successively with 1N aqueous sodium hydroxide solution, water and aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered off inorganic salt and concentrated under reduced pressure. The residue was purified by medium pressure preparative high performance liquid chromatography (hexane:ethyl acetate=30:1) to obtain phenyl N-(phenoxy)-3-(phenylthio)thioacrylimidate (0.14 g) as yellow oil.

1. temperatureunder ice-cooling
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. dissolutionThe residue was dissolved to ethanol (15 ml)
4. additionSodium salt of thiophenol (0.73 g) was added to the solution under ice-
5. temperaturecooling
6. temperatureheat
7. temperaturerefluxing for 2.5 hours
8. additiont-Butyl methyl ether (100 ml) was added to the reaction mixture
9. washwashed successively with 1N aqueous sodium hydroxide solution, water and aqueous saturated sodium chloride solution
10. dry with materialdried over anhydrous sodium sulfate
11. filtrationfiltered off inorganic salt
12. concentrationconcentrated under reduced pressure
13. customThe residue was purified by medium pressure preparative high performance liquid chromatography (hexane:ethyl acetate=30:1)

ORD record

ord-d59c685cb8a8453088f57463828955c4

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410316B2