Sodium Iodide → N-(4-((3-allyl-4-oxo-4,6-dihydro-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexane]-2-ylthio)methyl)phenyl)acetamide

HRID 1886902Notes

Reaction equation

HRID 1886902 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].[C:25]([NH:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1)(=[O:27])[CH3:26].[OH-].[K+].[I-].[Na+]>C(O)C.O>[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][CH2:33][C:32]1[CH:31]=[CH:30][C:29]([NH:28][C:25](=[O:27])[CH3:26])=[CH:36][CH:35]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 14797Potassium HydroxideHCID 148705Acetamide, N-(4-(chloromethyl)phenyl)-HCID 7188153-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one

Product 1

HCID 46870390N-(4-((3-allyl-4-oxo-4,6-dihydro-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexane]-2-ylthio)methyl)phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

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), 4-acetamidobenzyl chloride (0.060 g, 0.325 mmol), potassium hydroxide (0.025 g, 0.443 mmol), and catalytic sodium iodide (4.43 mg, 0.030 mmol) in ethanol (1.738 ml) was refluxed for 24 h. 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, DMSO-d6) δ ppm 9.95, 8.10, 7.51, 7.39-7.32, 5.85, 5.20, 5.13, 4.59-4.56, 3.02, 2.02, 1.70-1.67, 1.60-1.50, 1.28; MS (EI) m/z 486 (M+1)

Workup

  1. temperaturewas refluxed for 24 h
  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

Sources & evidence

ORD record
ord-5a84392f14b947c7bebbc5d1f31cc91f
Source dataset
uspto-grants-2013_08
Patent number
US08501722B2

Reaction notes

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