Hydrogen Peroxide → HCID 178425411, compound

HRID 1031371Notes

Reaction equation

HRID 1031371 reaction equation
[OH-].[K+].[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([Cl:11])[C:5]=1[NH:12][S:13]([C:16]1[N:26]=[C:19]2[N:20]=C(C)C=C(C)[N:18]2[N:17]=1)(=[O:15])=[O:14].OO.S(=O)(O)[O-].[Na+]>O>[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([Cl:11])[C:5]=1[NH:12][S:13]([C:16]1[N:26]=[C:19]([NH2:20])[NH:18][N:17]=1)(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 14155157(1,2,4)Triazolo(1,5-a)pyrimidine-2-sulfonamide, N-(2,6-dichloro-3-methylphenyl)-5,7-dimethyl-HCID 23665763Sodium Bisulfite

Product 1

HCID 178425411HCID 178425411, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
17 °C

Procedure

Potassium hydroxide (72.9 g of 85 percent pellets, 1.20 mol) was dissolved in one liter of water in a 2 liter round bottom flask and 113.3 g (0.30 mol) of wet N-(2,6-dichloro-3-methylphenyl)-5,7-dimethyl-1,2,4,-triazolo[1,5-a]pyrimidine-2-sulfonamide was added with stirring. The mixture obtained was cooled to 17° C. and 100 ml of 30 percent hydrogen peroxide solution (about 1 mole) was added with stirring over a 0.5 hour period so that the temperature did not exceed 40° C. The reaction was found to be complete after three hours by high pressure liquid chromatography. An aqueous solution of sodium bisulfite was added to quench the excess hydrogen peroxide and the solution obtained was filtered through celite and then acidified with concentrated hydrochloric acid. The precipitate that formed was collected by filtration, washed with water, and partially dried. This material, which is the N1 -acetyl derivative of the desired product, was dissolved in 800 ml of tetrahydrofuran and the resulting solution was combined with 100 ml of water and 100 ml of concentrated hydrochloric acid. This mixture was heated at reflux with stirring in a two liter round bottom flask overnight. The solvent was removed by evaporation under reduced pressure and the resulting aqueous suspension was filtered to collect the solid product. This was washed with water and dried to obtain 59.3 g (61 percent of theory) of the title compound as a white solid. This compound has an m.p. of 206°-8° C.

Workup

  1. customThe mixture obtained
  2. stirringwith stirring over a 0.5 hour period so that the temperature
  3. customdid not exceed 40° C
  4. customto quench the excess hydrogen peroxide
  5. customthe solution obtained
  6. filtrationwas filtered through celite
  7. customThe precipitate that formed
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. custompartially dried
  11. dissolutionwas dissolved in 800 ml of tetrahydrofuran
  12. temperatureThis mixture was heated
  13. temperatureat reflux
  14. stirringwith stirring in a two liter round bottom flask overnight
  15. customThe solvent was removed by evaporation under reduced pressure
  16. filtrationthe resulting aqueous suspension was filtered
  17. customto collect the solid product
  18. washThis was washed with water
  19. customdried

Sources & evidence

ORD record
ord-74098b1bc5e3450cabc18fb80220bc33
Source dataset
uspto-grants-1990_09
Patent number
US04954163

Reaction notes

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