Isatin → 1-Allylisatin

HRID 71046

Reaktionsgleichung

Reaktionsgleichung von HRID 71046
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[CH2:12](Cl)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:14]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3])[CH:13]=[CH2:12]

Komponenten

5

Edukt 3

HCID 7054IsatinHCID 7850Allyl chlorideHCID 11430Potassium Carbonate

Produkt 1

HCID 17135631-Allylisatin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A 500 mL flask is charged with isatin (50 g, 339 mmol), allyl chloride (33.8 g, 441 mmol), potassium carbonate (93.9 g, 679 mmol), and DMF (100 mL). The mixture is stirred at 70° C. for 14 hours (complete conversion by TLC), and then diluted with DMF. After filtration over a pad of cellite and removal of the solvent, the product remained as red crystals (68 g) which are used directly in the next step. 1HNMR (CDCl3, 300 MHz) δ 4.34 (dtr, 1H, 3J=5.3 Hz, 4J=1.8 Hz, NCH2CHC═CH2); 5.27 (dm, 1H, 3J=10.3 Hz, NCH2CHC═CHcis); 5.30 (dm, 1H, 3J=17.0 Hz, NCH2CHC═CHtrans); 5.82 (ddtr, NCH2CHC═CH2); 6.87 (d, 1H, 3J=7.9 Hz, H-7); 7.09 (br tr, 1H, 3J=7.3 Hz, H-5); 7.55 (dtr, 1H, 3J=8 Hz, H-6); 7.57 (d m, 1H, 3J=7.3 Hz, H-4). 13C-NMR (CDCl3, 75 MHz) δ 42.82 (NCH2); 111.11 (C-7); 117.77 (C-9); 118.80 (CH═CH2); 123.96 (C-5); 125.50 (C-4); 130.51 (CH═CH2); 138.48 (C-6); 150.96 (C-8); 158.02 (C-2); 183.29 (C-3).

Aufarbeitung

  1. filtrationAfter filtration
  2. customover a pad of cellite and removal of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-ef13f7fe59b6436297e671cc607c109d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822702B2

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