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

HRID 1164798Notes

Reaction equation

HRID 1164798 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[NH:3]1.[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:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:12])[NH:3][CH:2]2[CH3:1])=[O:24])([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 123607574-Methyl-3,4-dihydro-1H-quinazolin-2-oneHCID 14403282Methyl 4-chloro-3-methyl-4-oxobutanoate

Product 1

HCID 146206396-(3-Carbomethoxy-2-methyl-propionyl)-3,4-dihydro-4-methyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

3,4-Dihydro-4-methyl-2(1H)-quinazolinone (3.9 g) is added to a stirred suspension of anhydrous aluminum chloride (16.5 g) in carbon disulfide (120 ml) under nitrogen. 3-Carbomethoxy-2-methyl-propionyl chloride (4 g) is added dropwise to the stirred suspension, which is refluxed for about 17 hours and cooled to RT. The liquid phase is decanted and the residue is treated with ice/H2O (150 ml) and extracted with methylene chloride. The organic extract is dried, filtered, and concentrated in vacuo, affording the desired crude product as an oil, which is used in the next step without further purification.

Workup

  1. temperatureis refluxed for about 17 hours
  2. customThe liquid phase is decanted
  3. additionthe residue is treated with ice/H2O (150 ml)
  4. extractionextracted with methylene chloride
  5. extractionThe organic extract
  6. customis dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2730bdabea554667994afa5299d55c2b
Source dataset
uspto-grants-1990_03
Patent number
US04906630

Reaction notes

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