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Sodium hydride → 6,7-dichloro-2,3-dimethoxy-5-[5-(N,N-dimethylaminomethyl)-1,2,3-benzotriazol-1-ylmethyl]quinoxaline

HRID 1957132
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1957132
Cl.[CH3:2][N:3]([CH2:5][C:6]1[CH:14]=[CH:13][C:9]2[NH:10][N:11]=[N:12][C:8]=2[CH:7]=1)[CH3:4].[H-].[Na+].Br[CH2:18][C:19]1[C:28]([Cl:29])=[C:27]([Cl:30])[CH:26]=[C:25]2[C:20]=1[N:21]=[C:22]([O:33][CH3:34])[C:23]([O:31][CH3:32])=[N:24]2.[Cl-].[NH4+]>CN(C)C=O.O>[Cl:29][C:28]1[C:19]([CH2:18][N:10]2[C:9]3[CH:13]=[CH:14][C:6]([CH2:5][N:3]([CH3:2])[CH3:4])=[CH:7][C:8]=3[N:12]=[N:11]2)=[C:20]2[C:25](=[CH:26][C:27]=1[Cl:30])[N:24]=[C:23]([O:31][CH3:32])[C:22]([O:33][CH3:34])=[N:21]2
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Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 105459165-Bromomethyl-6,7-dichloro-2,3-dimethoxyquinoxalineHCID 178483163HCID 178483163, Verbindung

Produkt 1

HCID 543919756,7-dichloro-2,3-dimethoxy-5-[5-(N,N-dimethylaminomethyl)-1,2,3-benzotriazol-1-ylmethyl]quinoxalineAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

5-(N,N-Dimethylaminomethyl)-1H-1,2,3-benzotriazole hydrochloride (383 mg 1.8 mmol) was added to a suspension of sodium hydride (108 mg, 80% dispersion in oil, 3.6 mmol) in dry dimethylformamide (20 mL) at room temperature and stirred for 15 minutes. The mixure was cooled to -30° C., 5-bromomethyl-6,7-dichloro-2,3-dimethoxy quinoxaline (Preparation 1, 528 mg, 1.5 mmol) was added, and the mixture was stirred at -30° C. for 1 hour, and then allowed to warm slowly to 0° C. Saturated aqueous ammonium chloride (5 mL) was added, followed by water (50 mL). The product was extracted into ethyl acetate, the extracts were washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane/ethyl acetate, then ethyl acetate/methanol) to give 6,7-dichloro-2,3-dimethoxy-5-[5-(N,N-dimethylaminomethyl)-1,2,3-benzotriazol-1-yl] methylquinoxaline (135 mg, 28%), Rf =0.4 (silica gel, ethyl acetate/methanol=4:1), as the slowest eluted product isomer.

Aufarbeitung

  1. stirringthe mixture was stirred at -30° C. for 1 hour
  2. temperatureto warm slowly to 0° C
  3. extractionThe product was extracted into ethyl acetate
  4. washthe extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (
  8. washgradient elution with hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-895bcb967bc244aa8904eb75c5378bc3
Quelldatensatz
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05783572

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