Sulfuric Acid → 1-(Acetyloxy)-6-chloro-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine

HRID 1974035Notes

Reaction equation

HRID 1974035 reaction equation
[OH:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]=[C:3]1[C:12]([F:15])([F:14])[F:13].[C:16](OC(=O)C)(=[O:18])[CH3:17].S(=O)(=O)(O)O>>[C:16]([O:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]=[C:3]1[C:12]([F:15])([F:14])[F:13])(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 30824181-Hydroxyfluromidine

Product 1

HCID 203599201-(Acetyloxy)-6-chloro-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine

Conditions

Temperature
25 °C

Procedure

1-Hydroxy-6-chloro-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine (5 grams), 25 milliliters of acetic anhydride and 0.1 milliliter of sulfuric acid were mixed with stirring at 25° C. for fifteen minutes. The reaction mixture was then heated to reflux and refluxed for one-half hour, poured into ice with stirring, stirred for 10 minutes and filtered. Filtration yielded the desired 1-acetoxy-6-chloro-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine product as a solid. It was taken up in ether, dried over magnesium sulfate, and the ether evaporated. The product then melted at 103°-04° C.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux
  3. temperaturerefluxed for one-half hour
  4. additionpoured into ice
  5. stirringwith stirring
  6. stirringstirred for 10 minutes
  7. filtrationfiltered
  8. filtrationFiltration

Sources & evidence

ORD record
ord-a0fbe29d60fa43dfac9e85a740bb38e6
Source dataset
uspto-grants-1976_12
Patent number
US04000145

Reaction notes

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