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

HRID 1657667Notes

Reaction equation

HRID 1657667 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 20 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. additionpoured over ice cold aqueous HCl
  4. customAn oil separated
  5. customsubsequently crystallized on vigorous stirring
  6. customThis precipitate was removed by filtration
  7. dissolutiondissolved in ether
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customether removed by evaporation under vacuum
  11. distillationThe substance was purified by distillation
  12. customm.p., 33.5°-35.5°C.

Sources & evidence

ORD record
ord-4d60d7dfc1cf42bcbb9362f77361f22b
Source dataset
uspto-grants-1976_06
Patent number
US03961937

Reaction notes

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