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Triethylamine → 6-fluoro-2-(2-methoxyphenyl)-3H-quinazolin-4-one

HRID 2406172
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2406172
[C:1](Cl)(=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[NH2:12][C:13]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:14]=1[C:15]([NH2:17])=[O:16].C(N(CC)CC)C>O1CCCC1>[F:22][C:19]1[CH:18]=[C:14]2[C:13](=[CH:21][CH:20]=1)[N:12]=[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9])[NH:17][C:15]2=[O:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 102410032-Amino-5-fluorobenzamide

Produkt 1

HCID 1361214776-fluoro-2-(2-methoxyphenyl)-3H-quinazolin-4-oneAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

o-Anisoyl chloride (15.7 g, 92 mmol) was added dropwise to a solution of 2-amino-5-fluorobenzamide (13.0 g, 84 mmol) and triethylamine (16 mL, 110 mmol) in tetrahydrofuran (100 mL) cooled in an ice bath. Immediately a precipitate started forming. Stirring of the solution was continued for 5 hours at room temperature. The formed precipitate was collected by filtration and was washed twice with diethyl ether and dried at 50° C. in vacuo. The dried solid was suspended in 2 N aqueous sodium hydroxide solution (250 mL) and heated at reflux until a clear solution was obtained (3 hours). The reaction mixture was cooled to room temperature and filtered. The filtrate was acidified to pH<1 with concentrated aqueous HCl. The formed precipitate was collected by filtration and washed twice with water, twice with methanol, and twice with diethyl ether. The solid was dried in an oven at 45° C. to yield 6-fluoro-2-(2-methoxyphenyl)-3H-quinazolin-4-one (18.2 g, 80%) as a white solid.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customImmediately a precipitate started forming
  3. filtrationThe formed precipitate was collected by filtration
  4. washwas washed twice with diethyl ether
  5. customdried at 50° C. in vacuo
  6. temperatureheated
  7. temperatureat reflux until a clear solution
  8. customwas obtained (3 hours)
  9. filtrationfiltered
  10. filtrationThe formed precipitate was collected by filtration
  11. washwashed twice with water, twice with methanol
  12. customThe solid was dried in an oven at 45° C.

Quellen und Nachweise

ORD-Eintrag
ord-0f21f13161a849ec9dd1c4474b804ce6
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08809353B2

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