Ethanol → HCID 178527214, compound

HRID 1090324Notes

Reaction equation

HRID 1090324 reaction equation
[C:1]1([CH2:7][CH2:8][S:9][C:10]2[NH:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[N:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:24].C(=O)(O)[O-].[Na+].C(O)C>C(Cl)(Cl)Cl>[C:1]1([CH2:7][CH2:8][S:9]([C:10]2[NH:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[N:18]=2)=[O:24])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178420288HCID 178420288, compound

Product 1

HCID 178527214HCID 178527214, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-[(2-Phenylethyl)thio]-1H-imidazo[4,5-c]pyridine (2.4 g, 0.0094 mol) was dissolved in 120 mL of chloroform with heating. The reaction solution was cooled in an ice bath to 0°-5° C. m-Chloroperoxybenzoic acid (1.91 g, 0.0094 mol) was added portionwise. The reaction mixture was then stirred at room temperature for 1 hour. 10% aqueous sodium bicarbonate was added and the organic layer was separated and dried over magnesium sulfate. After filtering, the filtrate was evaporated to half the volume in a rotary evaporator. Ether was added to the cloudy point and the reaction mixture was cooled in ice. The crystals that had formed amounted to 0.63 g. An analytical sample, m.p. 171°-174° C., was obtained by recrystallization from ethanol.

Workup

  1. temperaturewith heating
  2. additionwas added portionwise
  3. customthe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtering
  6. customthe filtrate was evaporated to half the volume
  7. customin a rotary evaporator
  8. additionEther was added to the cloudy point
  9. temperaturethe reaction mixture was cooled in ice
  10. customThe crystals that had formed

Sources & evidence

ORD record
ord-49bd0b81e46a43c1808c311bdd0040f2
Source dataset
uspto-grants-1992_01
Patent number
US05081253

Reaction notes

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