Water → HCID 13646111, compound

HRID 979501Notes

Reaction equation

HRID 979501 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]1[NH:21][C:20](=[O:22])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[N:13]=1.[H-].[Na+].[CH3:26][N:27]([CH2:29][CH2:30]Cl)[CH3:28].O>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]1[N:21]([CH2:30][CH2:29][N:27]([CH3:28])[CH3:26])[C:20](=[O:22])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 135626413HCID 135626413, compound

Product 1

HCID 13646111HCID 13646111, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A suspension of 0.62 g (2 mmol) of 2-(2,5-dimethoxyphenylmethyl)-6-methyl-4(3H)-quinazolinone and 0.19 g (2 mmol) of 50% sodium hydride in dioxane (10 ml) were stirred at room temperature for 1 hour. Then, to the resulting reaction mixture was added 0.22 g (2 mmol) of dimethylaminoethyl chloride dissolved in dioxane (10 ml), followed by heating at 60° C. for 5 hours. After cooling, to the mixture obtained were added 30 ml of water. The resulting mixture was extracted with dichloromethane and the dichloromethane layer was concentrated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (eluent; dichloromethane: ethanol=97:3) to obtain 0.10 g (yield 13 %) of 2-(2,5-dimethoxyphenylmethyl)-3-(2-dimethylaminoethyl)-6-methyl-4(3H)-quinazolinone as an oily substance. The thus obtained quinazolinone was dissolved in ether and to the resulting solution was added a 5% hydrogen chloride-ethanol solution and the precipitated crystals were collected by filtration to obtain 2-(2,5-dimethoxyphenylmethyl)-3-(2-dimethylaminoethyl)-6-methyl-4(3H)-quinazolinone hydrochloride. The melting point and infrared absorption spectrum of this hydrochloride were identical with those of Compound 24 obtained in Example 24, respectively.

Workup

  1. customThen, to the resulting reaction mixture
  2. temperatureby heating at 60° C. for 5 hours
  3. temperatureAfter cooling, to the mixture
  4. customobtained
  5. extractionThe resulting mixture was extracted with dichloromethane
  6. concentrationthe dichloromethane layer was concentrated under reduced pressure
  7. customThe thus obtained residue was purified by silica gel column chromatography (eluent; dichloromethane: ethanol=97:3)

Sources & evidence

ORD record
ord-3a189fd69c744d9dbd5b7e7c588fb844
Source dataset
uspto-grants-1987_05
Patent number
US04668682

Reaction notes

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