Phthalyl-4-isothiocyanate → 5-Isothiocyanato-2-benzofuran-1,3-dione

HRID 1720188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720188
[N:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=O)=[C:2]=[S:3]>FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(Cl)Cl>[N:1]([C:4]1[CH:5]=[C:6]2[C:13](=[O:14])[O:15][C:8](=[O:10])[C:7]2=[CH:11][CH:12]=1)=[C:2]=[S:3]

Komponenten

4

Edukt 1

HCID 191815Phthalyl-4-isothiocyanate

Produkt 1

HCID 540346455-Isothiocyanato-2-benzofuran-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 9845Trifluoroacetic anhydrideLösungsmittel

Versuchsvorschrift

The 4-isothiocyanatophthalic acid thus obtained was immediately heated to reflux in a mixture of trifluoroacetic anhydride and methylene chloride for 2 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Recrystallization of the resultant solid from 30 mL of carbon tetrachloride afforded 4-isothiocyanatophthalic anhydride as brownish-purple crystals in a yield of 2.3778 g, (77 percent of theoretical). The title compound melted at 106°-108° C.; 1H NMR (300 MHz, acetone-d6) d, 8.15 (d, J=8.1 Hz, 1H), 8.06 (d, J=1.7 Hz, 1H), 7.97 (dd, J=8.1, 1.7 Hz, 1H); 13C NMR (75 MHz, acetone-d6) d 163.3, 162.6, 139.8, 134.8, 134.6, 130.6, 128.2, 123.5, 111.6; IR (CHCl3) 2010 (br), 1840, 1740 cm-1; MS m/e 205, 161, 133 (base), 74.

Aufarbeitung

  1. temperaturewas immediately heated
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customRecrystallization of the resultant solid from 30 mL of carbon tetrachloride

Quellen und Nachweise

ORD-Eintrag
ord-6170808c89b54db3afbd5bce63188d2e
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05505931

Notizen zur Reaktion

Wird geladen…