Ammonium Chloride → 9-Bromo-2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

HRID 1498098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1498098
C([Mg]Br)C.[Br:5][C:6]1[CH:21]=[CH:20][C:9]2[C:10]3[N:11]([C:15](I)=[C:16]([I:18])[N:17]=3)[CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1.[NH4+].[Cl-]>C(OCC)C.C1COCC1>[Br:5][C:6]1[CH:21]=[CH:20][C:9]2[C:10]3[N:11]([CH:15]=[C:16]([I:18])[N:17]=3)[CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 582047669-Bromo-5,6-dihydro-2,3-diiodoimidazo(1,2-d)(1,4)benzoxazepineHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 582048589-Bromo-2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepineAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 3.0 M solution of ethylmagnesium bromide in ethyl ether (1.1 mL) was added dropwise to a suspension of 9-bromo-2,3-diiodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (1.1 g, 2.2 mmol) in THF at −15° C. The mixture was stirred and followed by LC/MS. After 1 hour, there is no starting material left and the reaction was poured into sat. NH4Cl and extracted with ethyl acetate. The organic extracts were washed with water, brine, dried over MgSO4 and concentrated. The crude residue was purified by flash column chromatography to provide 9-bromo-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine as white solid (0.7 g).

Aufarbeitung

  1. waitleft
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0cd810e4384d4e49bc091e3d32956bf7
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09198918B2

Notizen zur Reaktion

Wird geladen…