Acetic Acid → HCID 14390404, compound

HRID 623033Notes

Reaction equation

HRID 623033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(O)(=[O:25])C.ClC1C=CC=C(C(OO)=O)C=1>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[C:11]3=[N+:12]([O-:25])[CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 70297m-Chloroperbenzoic acidHCID 14390220HCID 14390220, compound

Product 1

HCID 14390404HCID 14390404, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(4-chlorophenyl)-N,N-dimethyl-3H-imidazo[4,5-b]pyridine-3-acetamide (0.3 g, 0.00096 mole), glacial acetic acid (2.5 ml), and m-chloroperbenzoic acid (0.66 g, 0.00384 mole) was heated at 60° C. for a total of 4 hrs. The reaction mixture was diluted with water and the organic acid which precipitated was filtered. The aqueous filtrate was neutralized for peroxides with 10% sodium sulfite. The aqueous solution was evaporated to dryness and the residue was dissolved in methylene chloride. The methylene chloride was extracted with a minimum of saturated sodium bicarbonate. The methylene chloride was dried and evaporated to a residue which crystallized upon standing. The solid was recrystallized from tetrahydofuran-hexanes with refrigeration overnight. The solid was collected by filtration and dried under high vacuum overnight to give 0.28 g (88%) of the title compound mp. 200°-201.5° C.

Workup

  1. customthe organic acid which precipitated
  2. filtrationwas filtered
  3. customThe aqueous solution was evaporated to dryness
  4. dissolutionthe residue was dissolved in methylene chloride
  5. extractionThe methylene chloride was extracted with a minimum of saturated sodium bicarbonate
  6. dry with materialThe methylene chloride was dried
  7. customevaporated to a residue which
  8. customcrystallized
  9. customThe solid was recrystallized from tetrahydofuran-hexanes with refrigeration overnight
  10. filtrationThe solid was collected by filtration
  11. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-154c5f2d855e4f8e9ff8c9564f056a81
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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