Benzil → HCID 178420035, Verbindung

HRID 322018

Reaktionsgleichung

Reaktionsgleichung von HRID 322018
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:17]([C:21]1[NH:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1)[C:18]([NH2:20])=[NH:19]>C1C=CC=CC=1.N1C=CC=CC=1>[N:25]1[C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[NH:22][C:21]=1[N:17]=[C:18]1[NH:20][C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:20][C:18](=[N:17][C:21]3[NH:25][C:24]4[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=4[N:22]=3)[NH:19][C:9]2([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:19]1

Komponenten

5

Edukt 2

HCID 8651BenzilHCID 1785125941-(1H-benzimidazol-2-yl)guanidine

Produkt 1

HCID 178420035HCID 178420035, VerbindungAusbeute 17,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of benzil (1.05 g, 5.0 mmol) and 2-guanidinobenzimidazole (1.57 g, 9.0 mmol) in benzene (25 mL) was refluxed in pyridine (10 mL) for 1 h. After evaporating most of the pyridine under reduced pressure, the residue was treated with hot toluene and the resulting precipitate was filtered. The precipitate was then dissolved in 9:1 water:acetic acid (30 mL); the solution was filtered and the filtrate was neutralized to pH 7 with phosphate buffer. A precipitate formed, that was then collected and triturated with water to afford the title compound (0.42 g, 16%). 1H NMR (300 MHz, d6-DMSO) d 11.5 (br s, NH, 2 H), 10.0 (br s, NH, 2 H), 8.6 (br s, NH, 2 H), 7.28-7.10 (m, 14 H), 6.97 (dd, J=6.0, 3.0 Hz, 4 H); MS (ESI) m/z 525 [M+H]+; Anal. Calcd. for C30H24N10 . ½CH3CO2H ¾H2O: C, 65.37; H, 4.88; N, 24.65. Found: C, 65.36; H, 4.79; N, 24.48.

Aufarbeitung

  1. customAfter evaporating most of the pyridine under reduced pressure
  2. additionthe residue was treated with hot toluene
  3. filtrationthe resulting precipitate was filtered
  4. dissolutionThe precipitate was then dissolved in 9:1 water
  5. filtrationthe solution was filtered
  6. customA precipitate formed
  7. customthat was then collected
  8. customtriturated with water

Quellen und Nachweise

ORD-Eintrag
ord-0ff89d8a4ec7446ea87d3fe217c44e8c
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211200B1

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