2-Methoxyethyl isothiocyanate → 1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[2-methoxyethyl]thiourea

HRID 18146

Reaktionsgleichung

Reaktionsgleichung von HRID 18146
[NH2:1][C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:9]4[C:14]=2[C:13](=[O:16])[N:12]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:11](=[O:22])[C:10]=4[CH:23]=[CH:24][CH:25]=3)[CH:5]=[CH:4][CH:3]=1.[CH3:26][O:27][CH2:28][CH2:29][N:30]=[C:31]=[S:32]>C(#N)C>[CH3:21][N:19]([CH3:20])[CH2:18][CH2:17][N:12]1[C:11](=[O:22])[C:10]2[CH:23]=[CH:24][CH:25]=[C:8]3[C:9]=2[C:14](=[C:15]2[C:2]([NH:1][C:31]([NH:30][CH2:29][CH2:28][O:27][CH3:26])=[S:32])=[CH:3][CH:4]=[CH:5][C:6]2=[CH:7]3)[C:13]1=[O:16]

Komponenten

4

Edukt 2

HCID 1234752-Methoxyethyl isothiocyanateHCID 1006541311-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione

Produkt 1

HCID 167180391-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-[2-methoxyethyl]thiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

100 mg of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) (0.30 mmole) were dissolved in 6 ml of acetonitrile. 170 μl (5 molar equivalents) of 2-methoxyethyl isothiocyanate was added and the reaction mixture was maintained at 60° C. for 16 hours. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography (SiO2, CH2Cl2/MeOH 95/5). 125 mg of the desired product (formula shown hereinabove) were isolated as a red powder (yield=93%) which was characterized as follows:

Aufarbeitung

  1. customThe solvent was then evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8af1a32d928948288e3c791efb5cc3c4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741337B2

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