Water → 3-allyl-2-(4-methoxybenzylthio)-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one

HRID 1886900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1886900
[CH2:1]([N:4]1[C:18](=[O:19])[C:17]2[C:11]3([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:10][C:9]3[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=3[C:7]=2[NH:6][C:5]1=[S:24])[CH:2]=[CH2:3].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1.[OH-].[K+].O>C(O)C>[CH2:1]([N:4]1[C:18](=[O:19])[C:17]2[C:11]3([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[CH2:10][C:9]3[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=3[C:7]=2[N:6]=[C:5]1[S:24][CH2:31][C:30]1[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=1)[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 1650214-Methoxybenzyl bromideHCID 7188153-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one

Produkt 1

HCID 468702953-allyl-2-(4-methoxybenzylthio)-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1′-cyclohexan]-4(6H)-one (5, 0.100 g, 0.295 mmol), paramethoxybenzyl bromide (0.047 ml, 0.325 mmol), potassium hydroxide (0.025 g, 0.443 mmol) in Ethanol (1.738 ml) was refluxed overnight. 1 ml of water was added to the cooled reaction and the mixture was extracted with EtOAc 2×. The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. 1H NMR (500 MHz, CDCl3) δ ppm 8.17, 7.39-7.24, 6.88, 5.93, 5.31-5.26, 4.68, 4.57, 3.82, 3.07, 2.61, 1.75-1.72, 1.60-1.53, 1.43-1.37; MS (EI) m/z 459 (M+1)

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. extractionthe mixture was extracted with EtOAc 2×
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5104e10784e44714bd91a151ad1d2ff7
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501722B2

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