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Formic Acid → HCID 17816453, Verbindung

HRID 2249698
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2249698
Br[C:2]1[C:10]2[N:9]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:8](=[O:16])[N:7]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:6]=2[CH:5]=[C:4](Br)[C:3]=1[C:23]([O:25][CH3:26])=[O:24].C(O)=O.C(N(CC)CC)C.Cl>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)(=O)C>[CH2:17]([N:7]1[C:6]2[CH:5]=[CH:4][C:3]([C:23]([O:25][CH3:26])=[O:24])=[CH:2][C:10]=2[N:9]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:8]1=[O:16])[CH2:18][CH:19]([CH3:21])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 17816478HCID 17816478, Verbindung

Produkt 1

HCID 17816453HCID 17816453, VerbindungAusbeute 77,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In 7 ml of N,N-dimethylformamide are suspended 0.70 g of methyl 4,6-dibromo-1,3-diisopentyl-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylate, 0.16 g of tetrakis(triphenylphosphine)palladium(0), 0.44 ml of formic acid and 2.4 ml of triethylamine. The suspension is stirred at 100° C. for 3 hours. The reaction mixture is added to a mixture of ethyl acetate and water, pH is adjusted to 4 with 2 mol/L hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to obtain 0.37 g of methyl 1,3-diisopentyl-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylate as a colorless oily product.

Aufarbeitung

  1. customthe organic layer is separated
  2. customThe organic layer thus obtained
  3. washis washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-74901506a3a0406d9f6e947b3bde71a6
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07314888B1

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