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Sodium Iodide → 4-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-2-iodo-phenol

HRID 2251123
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Reaktionsgleichung

Reaktionsgleichung von HRID 2251123
[N:1]1[N:12]2[C:4]([N:5]=[C:6]3[C:10](=[C:11]2[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8][CH2:7]3)=[CH:3][CH:2]=1.[Na+].[I-:21].[OH-].[Na+].[O-]Cl.[Na+]>CO>[N:1]1[N:12]2[C:4]([N:5]=[C:6]3[C:10](=[C:11]2[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([I:21])[CH:14]=2)[CH2:9][CH2:8][CH2:7]3)=[CH:3][CH:2]=1
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Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 23665760Sodium HypochloriteHCID 1360572434-(6,7-Dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-phenol

Produkt 1

HCID 1360572424-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-2-iodo-phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-(6,7-Dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-phenol (500 mg, 0.002 mmol) was dissolved in methanol (10 mL) followed by addition of NaI (368 mg, 2.45 mmol) and NaOH (98 mg, 2.45 mmol). The solution was cooled to 0° C. followed by dropwise addition of NaOCl (5.25% aq, 3.8 ml) over 3 minutes. The reaction mixture was stirred at 0° C. for 1 hour followed by warming to room temperature and quenching with sodium thiosulphate (saturated. aq., 6 ml). The pH of the reaction was adjusted to ˜7 by addition of sodium dihydrogen phosphate. The solution was extracted with CH2Cl2. The organic layer was dried and concentrated. The residue was purified on silica gel (10%→60% EtOAc in hexane) to give 4-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-2-iodo-phenol.

Aufarbeitung

  1. temperatureby warming to room temperature
  2. customquenching with sodium thiosulphate (saturated. aq., 6 ml)
  3. additionThe pH of the reaction was adjusted to ˜7 by addition of sodium dihydrogen phosphate
  4. extractionThe solution was extracted with CH2Cl2
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (10%→60% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-39327a82a1a64bd882b580c972bcd673
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07319103B2

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