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

HRID 1886903Notes

Reaction equation

HRID 1886903 reaction equation
[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].C1(C)C=CC(S(O[CH2:35][CH2:36][O:37][CH3:38])(=O)=O)=CC=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][CH2:35][CH2:36][O:37][CH3:38])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 86977Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)HCID 7188153-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one

Product 1

HCID 468715253-allyl-2-(2-methoxyethylthio)-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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), 2-Methoxyethyl p-Toluenesulfonate (0.084 ml, 0.325 mmol), potassium hydroxide (0.025 g, 0.443 mmol) in Ethanol (1.738 ml) was refluxed ON. To the cooled solution, water (1 ml) was added and the mixture was extracted with EtOAc 2×. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to a yellow oil. The product was purified by flash column chromatography eluting with 0 to 2.5% EtOAc in hexane. 1H NMR (500 MHz, CDCl3) δ ppm 8.08, 7.39-7.23, 5.95, 5.33-5.28, 4.71, 3.79, 3.57, 3.45, 3.06, 2.61, 1.75-1.72, 1.60-1.54, 1.42-1.39; MS (EI) m/z 397 (M+1)

Workup

  1. temperaturewas refluxed ON
  2. extractionthe mixture was extracted with EtOAc 2×
  3. washThe organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow oil
  7. customThe product was purified by flash column chromatography
  8. washeluting with 0 to 2.5% EtOAc in hexane

Sources & evidence

ORD record
ord-160e32a4cfd940bbbedc91894b6ef089
Source dataset
uspto-grants-2013_08
Patent number
US08501722B2

Reaction notes

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