Aluminum(III) Chloride → 6-(3-Carbomethoxy-2-methyl-propionyl)-3,4-dihydro-1-methyl-2(1H)-quinazolinone

HRID 1164795Notes

Reaction equation

HRID 1164795 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][NH:4][C:3]1=[O:12].[Cl-].[Al+3].[Cl-].[Cl-].[C:17]([CH2:21][CH:22]([CH3:26])[C:23](Cl)=[O:24])([O:19][CH3:20])=[O:18]>C(=S)=S>[C:17]([CH2:21][CH:22]([CH3:26])[C:23]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:2]([CH3:1])[C:3](=[O:12])[NH:4][CH2:5]2)=[O:24])([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 14403282Methyl 4-chloro-3-methyl-4-oxobutanoateHCID 146206331-Methyl-1,2,3,4-tetrahydroquinazolin-2-one

Product 1

HCID 146206386-(3-Carbomethoxy-2-methyl-propionyl)-3,4-dihydro-1-methyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

3,4-Dihydro-1-methyl-2(1H)-quinazolinone (2.5 g) is added to a stirred suspension of anhydrous aluminum chloride (10.5 g) in carbon disulfide (120 ml) under nitrogen. 3-Carbomethoxy-2-methyl-propionyl chloride (2.5 g) is added dropwise to the stirred suspension, which is refluxed for about 18 hours and cooled to RT. The liquid phase is decanted and the residue treated with ice/H2O and 6N HCl (25 ml). The aqueous mixture is extracted with methylene chloride, the organic extract dried, filtered and concentrated in vacuo, affording the desired product as an oil which is used in the next step without further purification.

Workup

  1. temperatureis refluxed for about 18 hours
  2. customThe liquid phase is decanted
  3. additionthe residue treated with ice/H2O and 6N HCl (25 ml)
  4. extractionThe aqueous mixture is extracted with methylene chloride
  5. extractionthe organic extract
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-215e67e218bc40c382520a4e4918f03e
Source dataset
uspto-grants-1990_03
Patent number
US04906630

Reaction notes

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