2-Propanol, sodium salt (1:1) → HCID 18542103, compound

HRID 1267823Notes

Reaction equation

HRID 1267823 reaction equation
[CH3:1][CH:2]([CH3:4])[O-:3].[Na+].Cl[CH2:7][C:8]1[N:9]=[C:10]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:21]=2[C:22]([F:25])([F:24])[F:23])[O:11][C:12]=1[CH:13]1[CH2:15][CH2:14]1>CC(O)C>[CH:13]1([C:12]2[O:11][C:10]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[C:22]([F:25])([F:24])[F:23])=[N:9][C:8]=2[CH2:7][O:3][CH:2]([CH3:4])[CH3:1])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 109204432-Propanol, sodium salt (1:1)HCID 18542108HCID 18542108, compound

Product 1

HCID 18542103HCID 18542103, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A freshly prepared solution of sodium isopropoxide (20 mg of Na, 5 ml of 2-propanol) was added to a solution of 4-chloromethyl-5-cyclopropyl-2-(4-trifluoromethyl-3-pyridyl)-oxazole (200 mg) in 2-propanol (5 ml), and the mixture was heated under reflux for 10 hours. The reaction mixture was subsequently concentrated, mixed with water and extracted with dichloro-methane. The organic phase was washed with saturated sodium chloride solution, dried (MgSO4) and filtered through silica gel. Concentration of the organic phase gave the product in pure form as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 hours
  3. concentrationThe reaction mixture was subsequently concentrated
  4. additionmixed with water
  5. extractionextracted with dichloro-methane
  6. washThe organic phase was washed with saturated sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered through silica gel
  9. customConcentration of the organic phase gave the product in pure form as a pale yellow oil

Sources & evidence

ORD record
ord-60437206088a4488b4254812b8061c0e
Source dataset
uspto-grants-2003_04
Patent number
US06555501B1

Reaction notes

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