Acetic Acid → HCID 14390405, compound

HRID 2351694Notes

Reaction equation

HRID 2351694 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH2:20])=[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:23])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]([NH2:20])=[O:19])[C:11]3=[N+:12]([O-:23])[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 3082931Ahr 12245

Product 1

HCID 14390405HCID 14390405, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetamide (1.84 g, 0.0064 mole), glacial acetic acid, and m-chloroperbenzoic acid (4.4 g, 0.0256 mole) was heated at 60° C. for a total of 4 hours. 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 treated with methylene chloride/saturated sodium bicarbonate. The insoluble precipitate was filtered, washed with methylene chloride and water, and dried at 50° C. under high vacuum overnight to give 1.0 g (52%) of title compound, mp. 272°-75° C. with decomposition.

Workup

  1. customthe organic acid which precipitated
  2. filtrationwas filtered
  3. customThe aqueous solution was evaporated to dryness
  4. additionthe residue was treated with methylene chloride/saturated sodium bicarbonate
  5. filtrationThe insoluble precipitate was filtered
  6. washwashed with methylene chloride and water
  7. customdried at 50° C. under high vacuum overnight

Sources & evidence

ORD record
ord-522c89b31a444511a36638d5f042dd4d
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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