Ethanol → HCID 178441849, compound

HRID 486017Notes

Reaction equation

HRID 486017 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][CH:10]=[C:9]([C:16]([OH:18])=[O:17])[CH:8]=2)[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.[CH2:24](O)[CH3:25]>>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][CH:10]=[C:9]([C:16]([O:18][CH2:24][CH3:25])=[O:17])[CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 178441848HCID 178441848, compound

Product 1

HCID 178441849HCID 178441849, compound

Procedure

A mixture of 5.0 g of 2-butyl-7-carboxy-4(1H)-quinazolinone in 100 ml of absolute ethanol containing 2 ml of sulfuric acid is refluxed for 48 hours. The solvent is evaporated in vacuo and the residue partitioned between water and chloroform. The organic layer is washed with aqueous saturated sodium bicarbonate, dried with anhydrous sodium sulfate, filtered and evaporated to a residue which crystallizes from ethyl acetate-hexane to afford 4.5 g of the desired product, mp 145° C.

Workup

  1. temperatureis refluxed for 48 hours
  2. customThe solvent is evaporated in vacuo
  3. customthe residue partitioned between water and chloroform
  4. washThe organic layer is washed with aqueous saturated sodium bicarbonate
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated to a residue which
  8. customcrystallizes from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9eb425315bb84a048fb5e27cac5aa207
Source dataset
uspto-grants-1994_03
Patent number
US05290780

Reaction notes

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