Phosphorus pentachloride → HCID 22558186, compound

A 100 mg portion of 2-mercaptonaphtho[2,3-d]oxazole dissolved in 30 ml of anhydrous benzene was mixed with 130 mg of phosphorus pentachloride, and the mixture was refluxed under heating for 2 hours. To this was further added 90 mg of phosphorus pentachloride, followed by additional 2.5 hours of heating under reflux. Under cooling with ice, 995 mg of N-methylpiperazine was added to the resulting solution, and the reaction was carried out for 1 hour at the same temperature and then for 48 hours at room temperature. Precipitated materials in the reaction solution were removed by filtration, and the resulting filtrate was concentrated under a reduced pressure. The thus obtained residue was dissolved in 300 ml of ethyl acetate, washed three times with water, dehydrated with sodium sulfate and then concentrated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography (chloroform:methanol=50:1) to obtain 18 mg of the title compound.

1. temperaturethe mixture was refluxed
2. temperatureunder heating for 2 hours
3. temperatureof heating
4. temperatureunder reflux
5. additionwas added to the resulting solution
6. waitthe reaction was carried out for 1 hour at the same temperature
7. waitfor 48 hours at room temperature
8. customPrecipitated materials in the reaction solution were removed by filtration
9. concentrationthe resulting filtrate was concentrated under a reduced pressure
10. dissolutionThe thus obtained residue was dissolved in 300 ml of ethyl acetate
11. washwashed three times with water
12. concentrationconcentrated under a reduced pressure
13. customThe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=50:1)

ORD record

ord-b9e033506f0a4db2a84a923f414b11d0

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05631257