m-Chloroperbenzoic acid → HCID 178527207, compound

HRID 1090323Notes

Reaction equation

HRID 1090323 reaction equation
[C:1]1([CH2:7][S:8][C:9]2[NH:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:23]>C(Cl)(Cl)Cl.CO>[C:1]1([CH2:7][S:8]([C:9]2[NH:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:17]=2)=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178420433HCID 178420433, compound

Product 1

HCID 178527207HCID 178527207, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

To a chilled (0°-5° C.) solution of 3.3 g (0.014 mol) of 2-[[(phenyl)methyl]thio]-1H-imidazo[4,5-c]pyridine in 50 mL of chloroform and 5 mL of methanol was added dropwise a solution containing 2.78 g (0.014 mol) of m- chloroperoxybenzoic acid in 50 mL of chloroform. The reaction mixture was then stirred at room temperture for 45 minutes. Approximately one half of the chloroform was removed in a rotary evaporator and the reaction mixture was then poured into 200 mL of ether. The reaction mixture was cooled in ice. The precipitate that formed was collected and amounted to 1.78 g. The product was suspended in aqueous 10% sodium bicarbonate solution, filtered and was air dried overnight. The product amounted to 1.39 g. An analytical sample (m.p. 190°-193° C.) was obtained by recrystallization from ethanol.

Workup

  1. additionwas added dropwise a solution
  2. customApproximately one half of the chloroform was removed in a rotary evaporator
  3. additionthe reaction mixture was then poured into 200 mL of ether
  4. temperatureThe reaction mixture was cooled in ice
  5. customThe precipitate that formed
  6. customwas collected
  7. filtrationfiltered
  8. customdried overnight
  9. customAn analytical sample (m.p. 190°-193° C.) was obtained by recrystallization from ethanol

Sources & evidence

ORD record
ord-53dfd3426b544100bd425c6728cae632
Source dataset
uspto-grants-1992_01
Patent number
US05081253

Reaction notes

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