Water → HCID 178441846, compound

HRID 486493Notes

Reaction equation

HRID 486493 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([C:16]#[CH:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].O.S(=O)(=O)(O)[OH:20]>C(O)(=O)C>[C:16]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:14][C:13]2=[O:15])(=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 178435591HCID 178435591, compound

Product 1

HCID 178441846HCID 178441846, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1.20 of 2-butyl-6-ethynyl-4(1H)-quinazolinone in 90 ml of acetic acid is added 0.45 g of mercuric sulfate, 0.9 ml of water and 0.3 ml of sulfuric acid. The reaction mixture is heated at reflux for 5 hours, cooled to room temperature and quenched with 150 ml of water. The resulting mixture is concentrated in vacuo, diluted with 150 ml of water and extracted with 6:1 chloroform-reethanol. The combined organics are dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel, eluting with 1:1 ethyl acetate-hexanes to give 0.67 g of the desired product as a white solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 5 hours
  3. customquenched with 150 ml of water
  4. concentrationThe resulting mixture is concentrated in vacuo
  5. additiondiluted with 150 ml of water
  6. extractionextracted with 6:1 chloroform-reethanol
  7. dry with materialThe combined organics are dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by flash chromatography on silica gel
  11. washeluting with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-e0a03b2365cf47ef9d423242138effcd
Source dataset
uspto-grants-1994_03
Patent number
US05292734

Reaction notes

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