2-(Dimethylamino)ethanol → HCID 69960351, compound

HRID 1291408Notes

Reaction equation

HRID 1291408 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:10]1[CH:38]=[CH:37][C:13]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]3[N:33]([CH3:34])[C:32](=[O:35])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][C:30]=4[CH3:36])[N:25]=3)=[CH:18][CH:17]=2)=[O:15])=[CH:12][N:11]=1>CN(C=O)C>[CH3:34][N:33]1[C:32](=[O:35])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[CH3:36])[N:25]=[C:24]1[CH:23]=[CH:22][C:19]1[CH:20]=[CH:21][C:16]([C:14](=[O:15])[C:13]2[CH:37]=[CH:38][C:10]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:11][CH:12]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 73470985HCID 73470985, compound

Product 1

HCID 69960351HCID 69960351, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-dimethylaminoethanol (53 mg) in DMF (3 ml) was added 60% sodium hydride (29 mg) and the mixture was stirred at room temperature for 10 minutes. Then, 2-[2-[4-(6-chloronicotinoyl)phenyl]vinyl]-3,5-dimethyl-4(3H)-quinazolinone (208 mg) was added and the mixture was further stirred at room temperature for 2 hours. This reaction mixture was extracted with ethyl acetate and the organic layer was washed serially with water and saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated to 10 ml. To this organic was added 1N-hydrochloric acid (2 ml) and the mixture was extracted with water. The aqueous layer was diluted with saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated to dryness to provide 169 mg of yellow powder.

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 hours
  2. extractionThis reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed serially with water and saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to 10 ml
  6. additionTo this organic was added 1N-hydrochloric acid (2 ml)
  7. extractionthe mixture was extracted with water
  8. additionThe aqueous layer was diluted with saturated aqueous NaHCO3 solution
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with saturated aqueous NaCl solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c54bfb18ba944a1297f4a834708850c3
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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