Dibutyltin oxide → HCID 178431717, Verbindung

HRID 50705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50705
[CH3:1][C:2]1([CH3:21])[O:7][C:6](=[O:8])[NH:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])=[CH:12][C:3]1=2.C[Si]([N:26]=[N+:27]=[N-:28])(C)C.C([Sn](=O)CCCC)CCC>O1CCOCC1>[CH3:1][C:2]1([CH3:21])[O:7][C:6](=[O:8])[NH:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]3[CH:20]=[CH:19][CH:18]=[C:15]([C:16]4[NH:28][N:27]=[N:26][N:17]=4)[CH:14]=3)=[CH:12][C:3]1=2

Komponenten

5

Edukt 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 98142163-(4,4-Dimethyl-2-oxo-2,4-dihydro-1H-benzo[D][1,3]oxazin-6-YL)benzonitrile

Produkt 1

HCID 178431717HCID 178431717, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)benzonitrile (0.77 g, 2.8 mmol), trimethylsilyl azide (0.68 g, 5.6 mmol), and dibutyl tin oxide (0.071 g, 0.28 mmol) in dioxane (20 mL) was heated at reflux under a blanket of nitrogen. Upon completion of the reaction, the dioxane was removed, the organics taken up in ethyl acetate (100 mL), and washed with NaHCO3 (100 mL). The aqueous layer was acidified with 1 N aqueous HCl and extracted with ethyl acetate (100 mL). The organic layer was dried over MgSO4, and concentrated. Crystallization from ether (20 mL) gave 4,4-dimethyl-6-[3-(1H-tetrazol-5-yl)-phenyl]-1,4-dihydrobenzo[d][1,3]-oxazin-2-one as a light yellow solid (0.23 g, 26%): mp 238-240° C.; 1H-NMR (DMSO-d6) δ 10.4 (s, 1H), 8.3 (bs, 1H), 8.02 (d, 1H, J=7.66 Hz), 7.9 (d, 1H, J=7.91 Hz), 7.72-7.65 (m, 3H), 7.03 (d, 1H, J=8.75 Hz), 1.70 (s, 6H); MS (ESI) m/z 320 ([M−H]−, 100%), Anal. Calc. For C17H15N5O2: C, 63.54; H, 4.71; N, 21.79. Found: C, 62.16; H, 4.67; N, 21.31.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under a blanket of nitrogen
  3. customUpon completion of the reaction
  4. customthe dioxane was removed
  5. washwashed with NaHCO3 (100 mL)
  6. extractionextracted with ethyl acetate (100 mL)
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated
  9. customCrystallization from ether (20 mL)

Quellen und Nachweise

ORD-Eintrag
ord-27bc82d301e54460b07c1e7a7c4ee83a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713478B2

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