Carbon tetrabromide → HCID 68775340, Verbindung

HRID 1628572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628572
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[N:15]([CH2:16][CH2:17][CH2:18]O)[C:14]2[C:20]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:21][CH:22]=[CH:23][C:13]=2[N:12]=1)=[O:10].[Br:29]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C(OCC)(=O)C>[Br:29][CH2:18][CH2:17][CH2:16][N:15]1[C:14]2[C:20]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:21][CH:22]=[CH:23][C:13]=2[N:12]=[C:11]1[C:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])=[O:10]

Komponenten

6

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68764177HCID 68764177, Verbindung

Produkt 1

HCID 68775340HCID 68775340, VerbindungAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred suspension of (2,4-dichlorophenyl)[7-(diethylamino)-1-(3-hydroxypropyl)-1H-benzimidazol-2-yl]methanone (404 mg, 0.961 mmol) and tetrabromomethane (637 mg, 1.92 mmol) in acetonitrile was added triphenylphosphine (504 mg, 1.92 mmol). After 15 min, the reaction mixture was diluted with ethyl acetate, washed with aqueous sodium hydrogen carbonate and brine, dried over sodium sulfate, filtrated, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 0-30% ethyl acetate/n-hexane gradient mixture to afford the desired product as yellow solid (407 mg, 0.842 mmol), 88%).

Aufarbeitung

  1. washwashed with aqueous sodium hydrogen carbonate and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with a 0-30% ethyl acetate/n-hexane gradient mixture

Quellen und Nachweise

ORD-Eintrag
ord-9d00df0619b34260ade95375a06b22fd
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

Notizen zur Reaktion

Wird geladen…