Octanoyl chloride → 1-OCTANOYLOXY-6-CHLORO-2-(TRIFLUOROMETHYL)1H-IMIDAZO(4,5-b)PYRIDINE

HRID 441719Notes

Reaction equation

HRID 441719 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](Cl)(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>N1C=CC=CC=1>[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:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 8124Octanoyl chlorideHCID 30824181-Hydroxyfluromidine

Product 1

HCID 203599441-OCTANOYLOXY-6-CHLORO-2-(TRIFLUOROMETHYL)1H-IMIDAZO(4,5-b)PYRIDINE

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1-hydroxy-6-chloro-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine (2.37 grams) in 5 milliliters of pyridine was added octanoyl chloride (1.63 grams). The addition was carried out portionwise with stirring and resulted in the precipitation of a white solid. The reaction mixture was set on a steam bath for twenty minutes, then poured over ice cold aqueous HCl. An oil separated and subsequently crystallized on vigorous stirring. This precipitate was removed by filtration, dissolved in ether, dried over magnesium sulfate, filtered, and ether removed by evaporation under vacuum. The substance was purified by distillation, m.p., 33.5°-35.5° C.

Workup

  1. additionThe addition
  2. customresulted in the precipitation of a white solid
  3. waitThe reaction mixture was set on a steam bath for twenty minutes
  4. additionpoured over ice cold aqueous HCl
  5. customAn oil separated
  6. customsubsequently crystallized on vigorous stirring
  7. customThis precipitate was removed by filtration
  8. dissolutiondissolved in ether
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customether removed by evaporation under vacuum
  12. distillationThe substance was purified by distillation
  13. customm.p., 33.5°-35.5° C.

Sources & evidence

ORD record
ord-190d0b5943e0474998e509bec2b417c2
Source dataset
uspto-grants-1977_08
Patent number
US04042593

Reaction notes

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