Acetic Acid → 6-Bromo-1-cyclopentyl-2-methyl-1H-benzoimidazole

HRID 2264363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264363
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:15](OCC)(OCC)(OCC)[CH3:16].C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:15]([CH3:16])[N:9]([CH:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)[C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 66221Triethyl orthoacetateHCID 516892Sodium BicarbonateHCID 65343498HCID 65343498, Verbindung

Produkt 1

HCID 674280416-Bromo-1-cyclopentyl-2-methyl-1H-benzoimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Heat a mixture of 4-bromo-N2-cyclopentyl-benzene-1,2-diamine (10.6 g), triethyl orthoacetate (9.5 ml) and acetic acid (6.3 mL) at 100° C. for 2.5 h. Dilute with DCM and pour onto an aqueous saturated solution of sodium bicarbonate. Dry over sodium sulfate and remove the solvent under vacuum. Purify by silica gel column chromatography, eluting with DCM/ethanol-10% NH3 (0-3%) to afford 10.67 g of the title compound. MS (ES+): m/z=280 (M+H)+.

Aufarbeitung

  1. temperatureHeat
  2. dry with materialDry over sodium sulfate
  3. customremove the solvent under vacuum
  4. customPurify by silica gel column chromatography
  5. washeluting with DCM/ethanol-10% NH3 (0-3%)

Quellen und Nachweise

ORD-Eintrag
ord-9fbd4e68e311494495f5ca37f688c39e
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855211B2

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