Carbon Disulfide → 6-(3-Carbomethoxy-3-methyl-propionyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

HRID 1164797

Reaction equation

HRID 1164797 reaction equation
[CH3:1][N:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].[Cl-].[Al+3].[Cl-].[Cl-].[C:17]([CH2:21][CH:22](C)[C:23](Cl)=[O:24])([O:19][CH3:20])=[O:18].[C:27](=S)=S>>[C:17]([CH:21]([CH3:27])[CH2:22][C:23]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3](=[O:12])[N:2]([CH3:1])[CH2:11]2)=[O:24])([O:19][CH3:20])=[O:18]

Participants

5

Reactant 4

HCID 6348Carbon DisulfideHCID 38465583,4-Dihydro-3-methyl-2(1H)-quinazolinoneHCID 6451240Aluminum(III) ChlorideHCID 14403282Methyl 4-chloro-3-methyl-4-oxobutanoate

Product 1

HCID 198633366-(3-Carbomethoxy-3-methyl-propionyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

Procedure

3,4-Dihydro-3-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 H2O (120 ml) and extracted with methylene chloride. The organic extract is dried, filtered and concentrated in vacuo, affording the desired product as a solid, 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 H2O (120 ml)
  4. extractionextracted with methylene chloride
  5. extractionThe organic extract
  6. customis dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b15fd6128f214fdc99bb09dcde48ee29
Source dataset
uspto-grants-1990_03
Patent number
US04906630

Linked notes

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