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

HRID 1886901Notes

Reaction equation

HRID 1886901 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].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br.[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][CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[C:27]([O:26][CH3:25])[CH:28]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 7188153-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-oneHCID 40672073-Methoxybenzyl bromide

Product 1

HCID 468702963-allyl-2-(3-methoxybenzylthio)-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, 0.075 g, 0.222 mmol), 3-methoxybenzyl bromide (0.034 ml, 0.244 mmol), potassium hydroxide (0.019 g, 0.332 mmol) in Ethanol (1.303 ml) was refluxed overnight. To the cooled solution, water (1 ml) was added and the product was extracted with 10% MeOH in EtOAc, dried over sodium sulfate, and concentrated. The title compound was purified by flash column chromatography, eluting with 0 to 5% EtOAc in hexane. 1H NMR (500 MHz, CDCl3) δ ppm 8.15, 7.38-7.23, 7.06-7.02, 6.86-6.84, 5.945.32, 5.32-5.27, 4.69, 4.59, 3.77, 3.06, 2.60, 1.75-1.72, 1.60-1.54, 1.43-1.37; MS (EI) m/z 459 (M+1)

Workup

  1. temperaturewas refluxed overnight
  2. extractionthe product was extracted with 10% MeOH in EtOAc
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe title compound was purified by flash column chromatography
  6. washeluting with 0 to 5% EtOAc in hexane

Sources & evidence

ORD record
ord-fc63f2c805ef4c359fbecd145b4a8436
Source dataset
uspto-grants-2013_08
Patent number
US08501722B2

Reaction notes

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