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Sodium hydride → 4-(3,4-Dihydro-2H-chromen-4-yloxy)-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

HRID 2238579
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2238579
[OH:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[N:7]([CH3:12])[C:6]=2[CH:5]=[C:4]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH:3]=1.[H-].[Na+].Cl[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:24][CH2:23][CH2:22]1>CN(C)C=O>[O:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]([O:1][C:2]2[C:10]3[N:9]=[C:8]([CH3:11])[N:7]([CH3:12])[C:6]=3[CH:5]=[C:4]([C:13]([N:15]([CH3:16])[CH3:17])=[O:14])[CH:3]=2)[CH2:22][CH2:23]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 127921574-ChlorochromanHCID 534710164-Hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

Produkt 1

HCID 593038964-(3,4-Dihydro-2H-chromen-4-yloxy)-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamideAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a stirred suspension of 4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide (50 mg, 0.21 mmol, WO 2004054984) in N,N-dimethylformamide (2 mL) was added sodium hydride (60% dispersion in mineral oil, 11 mg, 0.27 mmol) at room temperature. After stirring for 20 minutes, a solution of 4-chlorochromane (71 mg, 0.42 mmol, WO 2000078751) in N,N-dimethylformamide (1 mL) was added at room temperature. The reaction mixture was warmed to 70° C., and stirred for 6 hours at the same temperature. The reaction mixture was quenched with sodium hydrogencarbonate aqueous solution, and extracted with ethyl acetate (20 mL×2). The combined extracts were washed with water and brine, dried over magnesium sulfate, and concentrated in vacuum. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol=10:1 as an eluent) to afford the title compound as a white solid (40 mg, 52%):

Aufarbeitung

  1. stirringstirred for 6 hours at the same temperature
  2. customThe reaction mixture was quenched with sodium hydrogencarbonate aqueous solution
  3. extractionextracted with ethyl acetate (20 mL×2)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6b7509b4db3a4ce399f3008ddcf73e92
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07718809B2

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