Sodium Chloride → 6-(2-oxopropyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

HRID 34904Notes

Reaction equation

HRID 34904 reaction equation
C([O:4][CH:5]([CH3:20])[CH:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[N:12]([CH3:19])[CH2:11]2)O)(=O)C.S(=O)(=O)(O)[O-].[K+].C(Cl)Cl.[Cl-].[Na+]>C(=O)(O)[O-].[Na+].O>[O:4]=[C:5]([CH3:20])[CH2:6][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[N:12]([CH3:19])[CH2:11]2

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6344DichloromethaneHCID 516920Potassium bisulfateHCID 142330486-(2-acetoxy-1-hydroxypropyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

Product 1

HCID 142330496-(2-oxopropyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 6-(2-acetoxy-1-hydroxypropyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone (6.47 g) prepared in Step 3 and potassium bisulfate (4.75 g) are ground together and placed under aspirator vacuum in an oil bath at 170° C. until all the material is a melt. Upon cooling the residue is partioned between methylene chloride (100 ml) and water (50 ml). The aqueous is diluted with 50 ml sat. sodium bicarbonate solution and sodium chloride (30 g) and then extracted with methylene chloride. The combined methylene chloride extracts are washed with sat. sodium bicarbonate, sat. aqueous sodium chloride solution, dried over Na2SO4, filtered and evaporated in vacuo. The residue dissolved in 5% methanol in chloroform was purified using flash chromotography on a silica gel column (230-400 mesh) to obtain pure 6-(2-oxopropyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone which was used in the next step.

Workup

  1. customplaced under aspirator vacuum in an oil bath at 170° C. until all
  2. temperatureUpon cooling the residue
  3. extractionextracted with methylene chloride
  4. washThe combined methylene chloride extracts are washed with sat. sodium bicarbonate, sat. aqueous sodium chloride solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. dissolutionThe residue dissolved in 5% methanol in chloroform
  9. customwas purified

Sources & evidence

ORD record
ord-c2c4c035fe7e4852818712180747a2f7
Source dataset
uspto-grants-1988_08
Patent number
US04764512

Reaction notes

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