Dimethylamine → HCID 49821537, Verbindung

HRID 74172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74172
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:26]=[CH:25][C:13]2[N:14]([CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:15]([CH2:17]O)=[N:16][C:12]=2[CH:11]=1.C(Cl)(=O)C(Cl)=O.[I-].[Na+].[CH3:35][NH:36][CH3:37]>CN(C)C=O.O1CCCC1.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:26]=[CH:25][C:13]2[N:14]([CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[C:15]([CH2:17][N:36]([CH3:37])[CH3:35])=[N:16][C:12]=2[CH:11]=1

Komponenten

8

Edukt 4

HCID 674DimethylamineHCID 5238Sodium IodideHCID 65578Oxalyl chlorideHCID 674979855-(Benzoxazol-2-yl)-2-hydroxymethyl-1-(tetrahydropyran-4-yl)benzimidazole

Produkt 1

HCID 49821537HCID 49821537, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

An eggplant flask (50 mL) equipped with a reflux condenser was charged with 5-(benzoxazol-2-yl)-2-hydroxymethyl-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 13) (0.055 g, 0.16 mmol), oxalyl chloride (0.024 g, 0.19 mmol), and anhydrous dichloromethane (3 mL), and after the addition of anhydrous N,N-dimethylformamide (5 drops) at room temperature, this was refluxed for 3.5 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. To the yellow residue was added anhydrous tetrahydrofuran (5 mL) and anhydrous sodium iodide (0.036 g, 0.24 mmol), followed by a tetrahydrofuran solution of dimethylamine (2.0 M, 3 mL), and this was refluxed for 14 hours. After being allowed to cool to room temperature, the solvent was distilled off under reduced pressure. The yellow residue (0.70 g) was purified by silica gel column chromatography (silica gel: 2.6 g; MeOH/CHCl3=1/5) to yield the title compound (0.026 g, 43% yield) as a pale yellow powder.

Aufarbeitung

  1. customAn eggplant flask (50 mL) equipped with a reflux condenser
  2. temperaturethis was refluxed for 3.5 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. temperaturethis was refluxed for 14 hours
  5. temperatureto cool to room temperature
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe yellow residue (0.70 g) was purified by silica gel column chromatography (silica gel: 2.6 g; MeOH/CHCl3=1/5)

Quellen und Nachweise

ORD-Eintrag
ord-d2bf71fe33954016a32f5e90f75fc8f9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

Notizen zur Reaktion

Wird geladen…