Dichloromethane → HCID 15425737, compound

In an atmosphere of argon, carbon tetrabromide (8.29 g, 25 mmol) and zinc powder (1.63 g, 25 mmol) were added in that order to a mixture of triphenylphosphine (6.56 g, 25 mmol) and dichloromethane (75 ml), and the mixture was stirred at room temperature for 23 hours. A dichloromethane (25 ml) solution of 3-formyl-10-methylphenothiazine (3.02 g, 12.5 mmol) was added and the mixture was again stirred for 7 hours. The reaction mixture was diluted with hexane and the insoluble matter was removed by filtration. The reaction product was extracted from the insoluble matter three times with hexane (about 60° C.), and the thus collected organic layers were combined and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:dichloromethane:hexane=10:10:80) to give the title compound (3.15 g, 7.93 mmol, 63%) as yellow crystals.

1. stirringthe mixture was again stirred for 7 hours
2. customthe insoluble matter was removed by filtration
3. extractionThe reaction product was extracted from the insoluble matter three times with hexane (about 60° C.)
4. concentrationconcentrated under a reduced pressure
5. customThe resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:dichloromethane:hexane=10:10:80)

ORD record

ord-ef7750ff920b464aa4fa1afbc4bc118d

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05830902