Stannous chloride dihydrate → 3-[2-(4-Amino-phenyl)-ethyl]-2-methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one

HRID 507402

Reaktionsgleichung

[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[C:5](=[O:18])[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1.O.O.Cl[Sn]Cl>C(O)C.O.N>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][N:6]2[C:5](=[O:18])[C:4]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:3]=[C:2]2[CH3:1])=[CH:14][CH:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture of 2-methyl-3-[2-(4-nitro-phenyl)-ethyl]-5,5-diphenyl-3,5-dihydro-imidazol-4-one (205 mg, 0.5 mmol) and SnCl2.2H2O (591 mg, 2.6 mmol) in 10 mL ethanol is heated to 50° C. for 5 hours. The reaction mixture is cooled to room temperature, diluted with water and aqueous ammonia is added to reach pH 8-9. The mixture is filtered, the filtrate evaporated and the residue purified by flash chromatography. ISCO Companion CombiFlash, 12 g silica gel, methylene chloride/ethanol to yield 3-[2-(4-amino-phenyl)-ethyl]-2-methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one (180 mg, 85%). LC/MS at 254 nm; [M+H] 370; Rt 2.424 min.

Aufarbeitung

temperatureThe reaction mixture is cooled to room temperature
additionis added
filtrationThe mixture is filtered
customthe filtrate evaporated
customthe residue purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-9d83dfe6cfc74659985b6b1d82a5ff24
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07786155B2

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