Triethylamine → 5-Isocyano-2,3-dihydroinden-1-one

HRID 230120

Reaktionsgleichung

Reaktionsgleichung von HRID 230120
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[CH:12](OCCCC)=O.C(N(CC)CC)C.O=P(Cl)(Cl)Cl>C1COCC1>[N+:1]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2)#[C-:12]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 11614Butyl FormateHCID 24813Phosphorus oxychlorideHCID 3128905-amino-2,3-dihydro-1H-inden-1-one

Produkt 1

HCID 187198135-Isocyano-2,3-dihydroinden-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-2,3-dihydroinden-1-one (5) and butyl formate (5 eq.) was allowed to reflux overnight. The reaction mixture was then concentrated to an oil which solidified upon standing. The crude material [N-(1-oxo-2,3-dihydro-1H-inden-5-yl)formamide (15.00 g, 73 mmol)] was suspended in cold (0° C.) THF (300 mL) and triethylamine (81 mL, 582 mmol). To this was slowly added 6.6 mL (1 eq.) of POCl3. HPLC after 2 hours showed almost complete conversion. The crude reaction mixture was added to silica gel and concentrated (the bath temp was kept at about 25° C.), and the concentrated mixture was loaded onto a silica column. The product was eluted with DCM (100%) to give 5-isocyano-2,3-dihydroinden-1-one (6).

Aufarbeitung

  1. temperatureto reflux overnight
  2. concentrationThe reaction mixture was then concentrated to an oil which
  3. customThe crude reaction mixture
  4. additionwas added to silica gel
  5. concentrationconcentrated (the bath temp
  6. customwas kept at about 25° C.
  7. washThe product was eluted with DCM (100%)

Quellen und Nachweise

ORD-Eintrag
ord-307d6a5571414fe3aa1b9374c2befa73
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566716B2

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