Sodium ethanethiolate → 5,7-dihydroxy-3-(4-hydroxyphenyl)-4(3H)-quinazolinone

HRID 130333Notes

Reaction equation

HRID 130333 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]([O:13]C)[CH:10]=[C:9]2[C:4]=1[C:5](=[O:23])[N:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=1)[CH:7]=[N:8]2.C([S-])C.[Na+]>CN(C=O)C>[OH:2][C:3]1[CH:12]=[C:11]([OH:13])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:23])[N:6]([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)[CH:7]=[N:8]2

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 116881915,7-Dimethoxy-3-(4-methoxyphenyl)quinazoline-4-one

Product 1

HCID 104232345,7-dihydroxy-3-(4-hydroxyphenyl)-4(3H)-quinazolinoneYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 100 mg (0.32 mmol) of 5,7-dimethoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinone as prepared in Example 18 or 19, and 524 mg (6.24 mmol) of sodium ethanethiolate in 2 ml of DMF was refluxed for 3.5 hr. DMF was evaporated and the residue dissolved in water. Concentrated HCl was added to adjust the pH to 5. The precipitate was filtered, dried and purified by chromatography on silica gel (loaded with CH2Cl2 and a slight amount of MeOH, eluted with 70% EtOAc in hexane) to yield 51 mg of 5,7-dihydroxy-3-(4-hydroxyphenyl)-4(3H)-quinazolinone (59%) as an off-white solid.

Workup

  1. temperaturewas refluxed for 3.5 hr
  2. customDMF was evaporated
  3. dissolutionthe residue dissolved in water
  4. additionConcentrated HCl was added
  5. filtrationThe precipitate was filtered
  6. customdried
  7. custompurified by chromatography on silica gel (
  8. washa slight amount of MeOH, eluted with 70% EtOAc in hexane)

Sources & evidence

ORD record
ord-9ae930638f1943b7b664b5b0bb346aba
Source dataset
uspto-grants-2008_06
Patent number
US07381730B2

Reaction notes

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