Trifluoroacetic acid → 7-methyl4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine

HRID 585444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585444
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:8][O:9][C:4]=2[CH:3]=1.FC(F)(F)C(O)=O.[N:25](OCCCC)=[O:26]>C(OCC)C>[CH3:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([N:25]=[O:26])[CH:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:8][O:9][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 10996Butyl nitriteHCID 109111697-methyl-3-phenyl-2H-1,4-benzoxazine

Produkt 1

HCID 223363397-methyl4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a mixture of 7-methyl-3-phenyl-2H-1,4-benzoxazine (22.5 g, 99.87 mmol) in ethyl ether (300 mL) is added trifluoroacetic acid (7.7 mL, 99.87 mmol). The resulting solution is chilled to 5° C. in an ice bath and n-butyl nitrite (12.26 mL, 99.87 mmol) is added dropwise. The mixture is stirred for 1 h; solids formed during the reaction. The solids are collected by filtration and washed with ether. The filtrates are partitioned between ether and water and the organic layers are washed three times with water (500 mL), dried over magnesium sulfate, and concentrated to dryness. The combined solids gave 23.22 g (97%) of 7-methyl-4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine.

Aufarbeitung

  1. customsolids formed during the reaction
  2. filtrationThe solids are collected by filtration
  3. washwashed with ether
  4. customThe filtrates are partitioned between ether and water
  5. washthe organic layers are washed three times with water (500 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e61060f5f7d143e5bb1390955ac9f605
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06932961B1

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