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

HRID 1886904Notes

Reaction equation

HRID 1886904 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].Br.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]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][CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])[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 457913472-Bromoethyldimethylammonium bromide

Product 1

HCID 468703913-allyl-2-(2-(dimethylamino)ethylthio)-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), beta-dimethylaminoethyl bromide hydrobromide (0.076 g, 0.325 mmol), potassium hydroxide (0.041 g, 0.739 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. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.12, 7.37-7.22, 5.95, 4.71, 3.48, 3.05, 2.76, 2.64-2.58, 2.36, 1.74-1.72, 1.59-1.53, 1.42-1.39; MS (EI) m/z 410 (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

Sources & evidence

ORD record
ord-5d379e6fa2354bd2bb2b694d8c799389
Source dataset
uspto-grants-2013_08
Patent number
US08501722B2

Reaction notes

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