Hydrogen Peroxide → Thiazolo[4,5-c]quinoline

HRID 1872606Notes

Reaction equation

HRID 1872606 reaction equation
[S:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[C:2]1S.[OH-].[Na+].OO>O.[OH-].[Na+]>[S:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 178527812HCID 178527812, compound

Product 1

HCID 3066778Thiazolo[4,5-c]quinolineYield 44.3%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Thiazolo[4,5-c]quinoline-2-thiol (8.7 g, 0.04 mole) was suspended in a solution of sodium hydroxide (1.4 g, 0.04 mole) in water. A few drops of 50% sodium hydroxide were added to the suspension until most of the solid dissolved. Hydrogen peroxide (13.5 mL of 30%, 0.08 mole) was added dropwise over a period of 30 minutes while maintaining the temperature of the reaction mixture at 25-35° C. with a cold water bath. The bath was removed and the reaction mixture was stirred for 15 minutes. Sulfuric acid (2.5 g of 95.98%) was added dropwise to the reaction mixture. After 30 minutes the reaction was made basic (pH 9-9.5) with 50% sodium hydroxide. The reaction mixture was acidified (pH 2.5) with hydrochloric acid, a tan solid precipitated. The mixture was then heated on a steam bath for 15 minutes and the precipitate dissolved. The solution was allowed to cool to ambient temperature and a precipitate formed. The mixture was made basic (pH 9) with 50% sodium hydroxide. The resulting oily product was extracted with ethyl acetate. The extracts were combined, washed with water, dried over magnesium sulfate and then concentrated under vacuum to provide 3.3 g of thiazolo[4,5-c]quinoline as a tan solid, m.p. 104.4-105° C. Analysis: Calculated for C10H6N2S: % C, 64.19; % H, 3.25; % N, 15.04; Found: % C, 64.15; % H, 3.26; % N, 14.9.

Workup

  1. dissolutiondissolved
  2. customThe bath was removed
  3. additionSulfuric acid (2.5 g of 95.98%) was added dropwise to the reaction mixture
  4. waitAfter 30 minutes the reaction was made basic
  5. customa tan solid precipitated
  6. temperatureThe mixture was then heated on a steam bath for 15 minutes
  7. dissolutionthe precipitate dissolved
  8. temperatureto cool to ambient temperature
  9. customa precipitate formed
  10. extractionThe resulting oily product was extracted with ethyl acetate
  11. washwashed with water
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-02918f4d164e4f98834710fd1db5d375
Source dataset
uspto-grants-2000_08
Patent number
US06110929

Reaction notes

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