Acetic Anhydride → HCID 178518031, Verbindung

HRID 2386921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2386921
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]([F:12])[C:3]=1[C:4]([NH2:6])=[O:5].S([O-])([O-])(=O)=O.[NH4+].[NH4+].[CH2:20](OC(OCC)OCC)C.C(OC(=O)C)(=O)C>>[F:12][C:7]1[CH:8]=[CH:9][C:10]([F:11])=[C:2]2[C:3]=1[C:4]([OH:5])=[N:6][CH:20]=[N:1]2

Komponenten

5

Edukt 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 6097028Ammonium SulfateHCID 592230322-Amino-3,6-difluorobenzamide

Produkt 1

HCID 178518031HCID 178518031, VerbindungAusbeute 92,3 %

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

2-Amino-3,6-difluorobenzamide (2.0 g, 11.6 mmol), ammonium sulfate (0.15 g, 1.16 mmol), triethylorthoformate (4.3 g, 4.8 mL, 29.1 mmol) and acetic anhydride (3.0 g, 2.8 mL, 29.1 mmol) were combined in a 100 mL round bottomed flask and the mixture heated to 145° C. on a heating mantle, becoming nearly homogeneous around 90° C., then precipitating additional solid. After 1 h, the mixture was cooled to room temperature and diluted with water and stirred. The precipitated solids were collected by filtration, washed with water and dried to give 1.95 g of 5,8-difluoroquinazolin-4-ol as a white solid. A second crop of 0.13 g was collected from the cold concentrated filtrate, 98% overall. M.P. 257-258° C., LC/MS (ESI) m/z 182, 1H NMR (300 MHz, d6-DMSO) δ 12.48 (bs, 1H), 8.13 (s, 1H), 7.70 (m, 1H), 7.27 (m, 1H).

Aufarbeitung

  1. custombecoming nearly homogeneous around 90° C.
  2. customprecipitating additional solid
  3. temperaturethe mixture was cooled to room temperature
  4. additiondiluted with water
  5. filtrationThe precipitated solids were collected by filtration
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dea32cc2f9744080b42fd26defc94522
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268843B2

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