2,1,3-Benzothiadiazol-5-yl isothiocyanate → 1-(2,1,3-Benzothiadiazol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}thiourea

HRID 18156

Reaktionsgleichung

Reaktionsgleichung von HRID 18156
[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.[N:26]1[S:27][N:28]=[C:29]2[CH:34]=[C:33]([N:35]=[C:36]=[S:37])[CH:32]=[CH:31][C:30]=12>C(#N)C>[N:26]1[S:27][N:28]=[C:29]2[CH:34]=[C:33]([NH:35][C:36]([NH:1][C:2]3[C:15]4[C:6](=[CH:7][C:8]5[C:9]6[C:14]=4[C:13](=[O:16])[N:12]([CH2:17][CH2:18][N:19]([CH3:20])[CH3:21])[C:11](=[O:22])[C:10]=6[CH:23]=[CH:24][CH:25]=5)[CH:5]=[CH:4][CH:3]=3)=[S:37])[CH:32]=[CH:31][C:30]=12

Komponenten

4

Edukt 2

HCID 27762922,1,3-Benzothiadiazol-5-yl isothiocyanateHCID 1006541311-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione

Produkt 1

HCID 167180991-(2,1,3-Benzothiadiazol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}thioureaAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

215 mg of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) (0.645 mmole) were dissolved in 10 ml of acetonitrile. 250 mg (2 molar equivalents) of 2,1,3-benzothiadiazol-5-yl isothiocyanate was added and the reaction mixture was maintained at room temperature 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). 303 mg of the desired product (formula shown hereinabove) were isolated as a red powder (yield=89%) which was characterized as follows:

Aufarbeitung

  1. customThe solvent was then evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2f157c282bce4bd8b9725903fcb26f59
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741337B2

Verknüpfte Notizen

Wird geladen…