2-Amino-1-benzylbenzimidazole → HCID 66850533, Verbindung

HRID 252201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252201
[Br:1][CH2:2][CH:3]([OH:12])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:13][C:14]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]=1>C1(C)C=CC=CC=1>[BrH:1].[CH2:19]([N:18]1[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH2:2][CH:3]([OH:12])[CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:14]1=[NH:13])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

4

Edukt 2

HCID 1707422-Amino-1-benzylbenzimidazoleHCID 113906081-bromo-3-phenoxy-propan-2-ol

Produkt 1

HCID 66850533HCID 66850533, VerbindungAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 1-bromo-3-phenoxy-propan-2-ol (5) (248 mg., 1.07 mmol.) in toluene (2 mL.) was added 2-amino-1-benzylbenzimidazole (3) (200 mg., 0.90 mmol) and the mixture was heated at reflux overnight under N2 gas. The reaction mixture was cooled to room temperature and filtered. Crystallization of the collected solid from isopropanol gave 1 as white crystals (85 mg., 23%). Recrystallization of the mother liquor afforded additional 1 as white crystals (70 mg., 19%). 1H-NMR (DMSO-d6) δ 4.12 (s, 2H), 4.33 (s, 1H), 4.43 (s, 2H), 5.57 (s, 2H), 6.96 (m, 3H), 7.21-7.38 (m, 10H), 7.46 (d, J=8.0 Hz, 1H), 7.62 (d, J=7.6 Hz, 1H), 9.18 (s, 2H); 13C-NMR (DMSO-d6) δ 45.58, 46.10, 66.54, 69.43, 110.53, 111.11, 120.71, 123.39, 123.47, 127.11, 127.91, 128.72, 129.39, 129.45, 130.39, 134.56, 150.27, 157.67, 158.33.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight under N2 gas
  3. filtrationfiltered
  4. customCrystallization of the collected solid from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-edebb761a8ae4ce5915cbf3f1036394c
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868028B2

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