Phenothiazine → Tert-butyl 3-(phenothiazin-10-ylmethyl)benzoate

HRID 1034074Notizen

Reaktionsgleichung

[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]([CH3:19])([O-:18])[CH3:17].[K+].Cl[CH2:22][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=1)[C:26](OC)=[O:27]>O1CCCC1>[CH:11]1[C:12]2[N:13]([CH2:22][C:23]3[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=3)[C:26]([O:18][C:16]([CH3:19])([CH3:17])[CH3:15])=[O:27])[C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[S:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of phenothiazine (1.00 g) in tetrahydrofuran (10 ml) was added potassium tert-butoxide (617 mg) at 0° C. The mixture was stirred at 0° C. for 20 minutes, and then a solution of methyl 3-(chloromethyl)benzoate (1.02 g) in tetrahydrofuran (10 ml) was added. The mixture was stirred at 25° C. for 3 hours, and then potassium tert-butoxide (1.02 g) was added. The mixture was stirred at 25° C. for 1 hour, and then evaporated. The residue was partitioned between ethyl acetate and 0.1N hydrochloric acid. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of .hexane and ethyl acetate (40:1) to give tert-butyl 3-(phenothiazin-10-ylmethyl)benzoate (598 mg) as crystals.

Aufarbeitung

stirringThe mixture was stirred at 25° C. for 3 hours
stirringThe mixture was stirred at 25° C. for 1 hour
customevaporated
customThe residue was partitioned between ethyl acetate and 0.1N hydrochloric acid
washThe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was chromatographed on silica gel eluting with a mixture of

Quellen und Nachweise

ORD-Eintrag: ord-a36674cce86e46d7ab7d6c66c5a80ab4
Quelldatensatz: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05312829

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