2-(Tributylstannyl)-1,3-thiazole → 4,4-Dimethyl-6-(3-thiazol-2-yl-phenyl)1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 50722

Reaktionsgleichung

Reaktionsgleichung von HRID 50722
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:20]=[CH:19][C:11]3[NH:12][C:13](=[O:18])[O:14][C:15]([CH3:17])([CH3:16])[C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:26]1[S:27][CH:28]=[CH:29][N:30]=1)CCC>CN(C=O)C>[CH3:16][C:15]1([CH3:17])[O:14][C:13](=[O:18])[NH:12][C:11]2[CH:19]=[CH:20][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:26]4[S:27][CH:28]=[CH:29][N:30]=4)[CH:3]=3)=[CH:9][C:10]1=2

Komponenten

4

Edukt 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 98624116-(3-Bromo-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Produkt 1

HCID 98589994,4-Dimethyl-6-(3-thiazol-2-yl-phenyl)1,4-dihydro-benzo[d][1,3]oxazin-2-oneAusbeute 23,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 6-(3-bromo-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (0.25 g, 0.75 mmol), tri-n-butyl-thiazol-2-yl tin (0.5 g, 1.3 mmol) in DMF (5 mL) was degassed to remove oxygen and then heated under nitrogen at 90° C. for 3 hours. The reaction mixture was cooled to rt and treated with ice-water (70 mL). Ethyl acetate (100 mL) was added and organic layer was separated, washed with brine, and dried (MgSO4). After removal of solvent, the residue was purified by a silica gel column (hexane:ethyl acetate/1:1) to give the title compound as a white solid (60 mg, 23%): mp 223-224° C.; 1H-NMR (DMSO-d6) δ10.4 (s, 1H), 9.13 (s, 1H), 8.45 (s, 1H), 7.94 (bs, 1H), 7.67-7.61 (m, 4H), 7.53 (t, 1H, J=7.68 Hz), 7.00 (d, 1H, J=8.81 Hz), 1.7 (s, 6H); MS (APCI) m/z 337([M+H]+, 100%), Anal. Calc. For C19H16N2O2S.0.25 H2O: C, 66.94; H, 4.88; N, 8.22. Found: C, 66.57; H, 4.65; N, 7.92.

Aufarbeitung

  1. customwas degassed
  2. customto remove oxygen
  3. temperatureThe reaction mixture was cooled to rt
  4. additiontreated with ice-water (70 mL)
  5. additionEthyl acetate (100 mL) was added
  6. customorganic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customAfter removal of solvent
  10. customthe residue was purified by a silica gel column (hexane:ethyl acetate/1:1)

Quellen und Nachweise

ORD-Eintrag
ord-20ad7ee9eaaf48c1a0c4a1b1893040a6
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713478B2

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