Water → HCID 57786269, Verbindung

HRID 1628944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628944
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:22](OC)=[O:23])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[CH2:12][CH2:13][N:7]21.[CH:26]1([Mg]Br)[CH2:28][CH2:27]1.O.O1[CH2:36][CH2:35][CH2:34]C1>>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:14]4[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=4[Cl:21])[CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([C:22]([CH:34]2[CH2:35][CH2:36]2)([CH:26]2[CH2:28][CH2:27]2)[OH:23])=[CH:4][CH:3]=1

Komponenten

5

Edukt 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 57786058HCID 57786058, VerbindungHCID 178418630HCID 178418630, Verbindung

Produkt 1

HCID 57786269HCID 57786269, VerbindungAusbeute 57 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of methyl 8-chloro-1-(2,4-dichlorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole-5-carboxylate (100 mg, 0.25 mmol) in tetrahydrofuran (2.5 mL) was added a solution of cyclopropyl magnesium bromide in tetrahydrofuran (1.0 M, 1.5 mL, 1.5 mmol) at 0° C. The mixture was stirred at 60° C. for 1.5 hr. Water was added to the reaction mixture at room temperature and the mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was passed through the silica gel pad eluting with ethyl acetate and recrystallized from ethyl acetate to give the title compound (64.4 mg, 0.144 mmol, 57%) as colorless crystals.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washOrganic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. washeluting with ethyl acetate
  6. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5841cf1739d74f24bcf946c673719131
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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