Trimethyl orthobeznoate → 1-Benzyl-5-bromo-2-phenyl-1H-benzo[d]imidazole

HRID 643405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643405
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](S(O)(=O)=O)=[CH:6][CH:7]=1.O.[CH2:13]([NH:20][C:21]1[C:22]([NH2:28])=[CH:23][C:24]([Br:27])=[CH:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.COC(OC)(OC)C1C=CC=CC=1>C(Cl)Cl>[CH2:1]([N:20]1[C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=2[N:28]=[C:13]1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 69720Trimethyl orthobeznoateHCID 521998p-Toluenesulfonic acid monohydrateHCID 289029062-Benzylamino-5-bromoaniline

Produkt 1

HCID 591330541-Benzyl-5-bromo-2-phenyl-1H-benzo[d]imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

p-TsOH.H2O (311.7 mg, 1.606 mmol) was added to a DCM (50 ml) solution of N1-benzyl-4-bromobenzene-1,2-diamine (4451 mg, 16.06 mmol) and trimethyl orthobenzoate (3096 μl, 17.66 mmol) and the resulting mixture was stirred at rt under an atmosphere of Nitrogen for 40 h. The reaction mixture was then concentrated in vacuo to give a yellow solid which was triturated with 40% MeOH/water (375 mL), filtered, washed with saturated NaHCO3 (20 ml)+H2O (80 ml) twice and 40% MeOH/H2O (2×50 ml), and dried to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm=5.44 (s, 2H), 7.05-7.08 (m, 3H), 7.30-7.36 (m, 4H), 7.44-7.50 (m, 3H), 7.66-7.68 (m, 2H) and 7.99 (dd, 1H, J=0.4 & 1.6 Hz). MS(ES+): m/z 363.20 and 365.26[MH+].

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customto give a yellow solid which
  3. customwas triturated with 40% MeOH/water (375 mL)
  4. filtrationfiltered
  5. washwashed with saturated NaHCO3 (20 ml)+H2O (80 ml) twice
  6. dry with material40% MeOH/H2O (2×50 ml), and dried

Quellen und Nachweise

ORD-Eintrag
ord-00aa2948276b4247834d88cfb77ea88b
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700594B2

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