Water → 1-Benzyl-1H-benzo[d]imidazol-2(3H)-one

HRID 2229423

Reaktionsgleichung

Reaktionsgleichung von HRID 2229423
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[C:17](Cl)([O:19]C(=O)OC(Cl)(Cl)Cl)Cl.O>ClCCl>[CH:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:8]2[C:17](=[O:19])[NH:1][C:2]3[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 94429TriphosgeneHCID 2735482N1-Benzylbenzene-1,2-diamine

Produkt 1

HCID 7365051-Benzyl-1H-benzo[d]imidazol-2(3H)-oneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

[N-(2-Aminophenyl)]-benzylamine (15.1 mmol, 3.0 g) in dichloromethane (80 ml) is charged with triphosgene (5.3 mmol, 1.57 g) in dichloromethane (40 ml) and is stirred at room temperature over the weekend. The suspension is poured into water (100 g) and is extracted with dichloromethane (2×50 ml). The organic layer is a suspension The colorless solid is filtered off, is dried in vacuo and is recrystallized from ethyl acetate to give the title product (81%)(R1=H, R2=benzyl, n=0).

Aufarbeitung

  1. extractionis extracted with dichloromethane (2×50 ml)
  2. filtrationis filtered off
  3. customis dried in vacuo
  4. customis recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8ced66928dcb40ffa410b7fe06355873
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420410B1

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