Hydrogen Peroxide → HCID 178527208, compound

HRID 1090319Notes

Reaction equation

HRID 1090319 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH2:9][S:10][C:11]2[NH:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[N:19]=2)[CH:6]=[CH:7][CH:8]=1.[Se](=O)=[O:23].OO.O>C(O)C>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[C:5]([CH2:9][S:10]([C:11]2[NH:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[N:19]=2)=[O:23])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962Water2×HCID 24007Selenium DioxideHCID 178506164HCID 178506164, compound

Product 1

HCID 178527208HCID 178527208, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-[[[3-(Trifluoromethyl)phenyl]methyl]thio]-1H-imidazo[4,5-c]pyridine (0.91 g, 0.0029 mol) was dissolved in 10 mL of ethanol. An oxidizing solution was prepared by dissolving 0.32 g (0.0029 mol) of selenium dioxide in 17 mL of ethanol by heating and adding 0.33 g (0.0029 mol) of 30% hydrogen peroxide and 0.25 mL of water. The oxidizing solution was added dropwise to the sulfide solution and the reaction mixture was stirred overnight at room temperature. Water (20 mL) was added to the reaction mixture which was then extracted with chloroform (3×25 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated to dryness. The residue amounted to 0.65 g. Purification by HPLC gave a product which on recrystallization from ethanol had a m.p. 194°-197° C.

Workup

  1. customAn oxidizing solution was prepared
  2. temperatureby heating
  3. extractionwas then extracted with chloroform (3×25 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by HPLC
  8. customgave a product which
  9. customon recrystallization from ethanol

Sources & evidence

ORD record
ord-eff100033a19414b9633a25ab9df90d8
Source dataset
uspto-grants-1992_01
Patent number
US05081253

Reaction notes

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