Acetic Acid → 6-(2-acetoxypropionyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

HRID 34903Notes

Reaction equation

HRID 34903 reaction equation
Br[CH:2]([CH3:17])[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[N:9]([CH3:16])[CH2:8]2)=[O:4].[C:18]([O-:21])(=[O:20])[CH3:19].[K+].C(O)(=O)C>O>[C:18]([O:21][CH:2]([CH3:17])[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[N:9]([CH3:16])[CH2:8]2)=[O:4])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517044Potassium AcetateHCID 138271666-(2-Bromopropionyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

Product 1

HCID 142330476-(2-acetoxypropionyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-(2-bromopropionyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone (2 g) prepared in Step 1, potassium acetate (2.64 g) and glacial acetic acid (20 ml) is refluxed for three hours. The reaction mixture is diluted with water and extracted with methylene chloride (3×50 ml) and the combined organic layers are washed with saturated aqueous sodium bicarbonate, dried, filtered and concentrated to obtain 6-(2-acetoxypropionyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone which is used in the next step.

Workup

  1. temperatureis refluxed for three hours
  2. extractionextracted with methylene chloride (3×50 ml)
  3. washthe combined organic layers are washed with saturated aqueous sodium bicarbonate
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-67471646d3cb497f94e1a58e2084f24a
Source dataset
uspto-grants-1988_08
Patent number
US04764512

Reaction notes

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