Hydrochloric Acid → HCID 11695088, compound

HRID 130335Notes

Reaction equation

HRID 130335 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]([O:14]C)[CH:11]=[C:10]2[C:5]=1[C:6](=[O:24])[N:7]([C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=1)[CH:8]=[N:9]2)[CH3:2].C([S-])C.[Na+].Cl>CN(C)C=O.O>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:10]2[C:5]=1[C:6](=[O:24])[N:7]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH:8]=[N:9]2)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4459711Sodium ethanethiolate2×HCID 11558899HCID 11558899, compound

Product 1

HCID 11695088HCID 11695088, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-ethoxy-7-methoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinone (0.0080 g, 0.0245 mmol), as prepared in Example 41, in dimethylformamide (0.25 mL), was added sodium ethanethiolate (0.0047 g, 0.0563 mmol). The resulting suspension was warmed to 120° C. to form a solution. After each hour (for 7 hours) additional sodium ethanethiolate (0.0047, 0.0563 mmol) was added. After 7 hrs, the cloudy orange reaction solution was cooled to room temperature and diluted with water (0.75 mL). The resulting yellow solution was acidified with 1.0N HCl to pH 3 wherein the reaction solution became cloudy. Extraction was performed with EtOAc (3×) and dichloromethane (3×). The combined organic layers were washed with brine (1×), dried over MgSO4, filtered, and concentrated. Column chromatography (5% MeOH in CH2Cl2) gave 0.0017 g (23%) of 5-ethoxy-7-hydroxy-3-(4-hydroxyphenyl) quinazoline-4-one, as a white solid.

Workup

  1. customto form a solution
  2. temperaturethe cloudy orange reaction solution was cooled to room temperature
  3. extractionExtraction
  4. washThe combined organic layers were washed with brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-03383af35d094e76824ae5e5a19e5764
Source dataset
uspto-grants-2008_06
Patent number
US07381730B2

Reaction notes

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