Formaldehyde → 4-oxo-4H-3,1-benzoxazine-8-carboxylic acid

HRID 1842856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842856
[NH2:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:14]=O>>[O:5]=[C:4]1[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([OH:13])=[O:12])[C:2]=2[N:1]=[CH:14][O:6]1

Komponenten

3

Edukt 2

HCID 712FormaldehydeHCID 2929162-Aminoisophthalic acid

Produkt 1

HCID 676086644-oxo-4H-3,1-benzoxazine-8-carboxylic acidAusbeute 89 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

2-Aminoisophthalic acid moiety (50.0 g; 276.0 mmol) and formaldehyde (250.0 ml; 5.00 V) were combined and heated to 140° C. for 4 h. The reaction mixture was cooled to room temperature and distilled under high vacuum on the rotary evaporator. The remaining formaldehyde was removed by azeotropic distillation with toluene. The residue was slurried with ethyl ether, filtered, and the solid was dried under vacuum to provide the desired intermediate (50.3 g, 89% yield).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. distillationdistilled under high vacuum on the rotary evaporator
  3. customThe remaining formaldehyde was removed by azeotropic distillation with toluene
  4. filtrationfiltered
  5. customthe solid was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-aa8514ff7c944df383ff18272029e126
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946247B2

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