Methanol → 5-Bromo-1,3-dihydro-2H-benzimidazol-2-one

HRID 2096793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2096793
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([NH2:21])[CH:15]=1.CO.O>CN1C(=O)CCC1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]2[NH:20][C:1](=[O:2])[NH:21][C:16]=2[CH:15]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 3235934-Bromobenzene-1,2-diamine

Produkt 1

HCID 122280605-Bromo-1,3-dihydro-2H-benzimidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1,1′-Carbonyldiimidazole (2.1 g) in NMP (5 ml) was added to a solution of 4-bromo-o-phenylenediamine (CAS Reg. No. 1575-37-7, 2 g) in NMP (5 ml). The mixture was heated to 100° C. for 2 h and then allowed to cool to 60° C. MeOH (3 ml) was added, and the mixture was allowed to cool to room temperature. Water (50 ml) was added. The mixture was filtered. The residue was washed with isopropanol and then dried in vacuo to give the title compound (1.65 g) as a dark brown solid. MS (m/e, ISP neg. ion)=213.1 [M−H+].

Aufarbeitung

  1. temperatureto cool to 60° C
  2. temperatureto cool to room temperature
  3. filtrationThe mixture was filtered
  4. washThe residue was washed with isopropanol
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5eb3a45532c3471dae728e3d279d97a0
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450313B2

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