m-Chloroperbenzoic acid → HCID 178490215, compound

HRID 1090325Notes

Reaction equation

HRID 1090325 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][S:11][C:12]2[NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[N:20]=2)[CH:6]=[CH:7][CH:8]=1.ClC1C=C(C=CC=1)C(OO)=[O:26].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][S:11]([C:12]2[NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[N:20]=2)=[O:26])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178490213HCID 178490213, compound

Product 1

HCID 178490215HCID 178490215, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-[[(3-Methoxyphenyl)ethyl]thio]-1H-imidazo[4,5-c]pyridine (4.0 g, 0.014 mol) was dissolved in 60 mL of chloroform and cooled in an ice bath to 0°-5° C. m-Chloroperoxybenzoic acid (3.13 g, 0.015 mol) was added in portions to the reaction mixture. After 45 minutes, 10% aqueous sodium bicarbonate solution was added. The organic layer was removed and dried over magnesium sulfate, filtered and evaporated to dryness in a rotary evaporator. The crude product (4.2 g) when subjected to HPLC gave 2.3 g of pure product, m.p. 125°-128° C.

Workup

  1. additionwas added in portions to the reaction mixture
  2. customThe organic layer was removed
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness in a rotary evaporator

Sources & evidence

ORD record
ord-53782033b9fb47769f7eb43b59c715f8
Source dataset
uspto-grants-1992_01
Patent number
US05081253

Reaction notes

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