Ammonium Chloride → 6-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 403160Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403160
[Cl-].[NH4+].[F:3][C:4]1([F:22])[O:9][C:8]2[CH:10]=[C:11]([F:17])[C:12]([N+:14]([O-])=O)=[CH:13][C:7]=2[N:6]([CH2:18][C:19]#[CH:20])[C:5]1=[O:21]>O.CO.O1CCCC1.[Fe]>[NH2:14][C:12]1[C:11]([F:17])=[CH:10][C:8]2[O:9][C:4]([F:3])([F:22])[C:5](=[O:21])[N:6]([CH2:18][C:19]#[CH:20])[C:7]=2[CH:13]=1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 871738852,2,7-trifluoro-6-nitro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

Produkt 1

HCID 866695376-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 962WaterLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To ammonium chloride (3.96 g, 74.0 mmol) in water was added iron powder (325 mesh; 4.13 g, 74.0 mmol). To the resulting mixture was added 2,2,7-trifluoro-6-nitro-4-(prop-2-ynyl)-2Hbenzo[b][1,4]oxazin-3(4H)-one (7.06 g, 24.67 mmol) in methanol/tetrahydrofuran. The resulting mixture was stirred vigorously at 70° C. for 2 hours. The reaction was quenched in water/ethyl acetate under stirring. The resulting 2 phase system was filtered and the layers were separated. The water layer was subsequently extracted with ethyl acetate. The combined organic phases were washed with brine, dried with Na2SO4 and concentrated to yield 5.15 g of the title compound. GCMS m/e (M+)=256

Aufarbeitung

  1. customThe reaction was quenched in water/ethyl acetate
  2. stirringunder stirring
  3. filtrationThe resulting 2 phase system was filtered
  4. customthe layers were separated
  5. extractionThe water layer was subsequently extracted with ethyl acetate
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-da77a239c4c046fcaa4283e31d9723ce
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748348B2

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