Ethanol → HCID 178441849, compound

HRID 1654134Notes

Reaction equation

HRID 1654134 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-515f65363d7349819ddc48547a43c247
Source dataset
uspto-grants-1995_04
Patent number
US05405849

Reaction notes

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