Hydrochloric Acid → HCID 18546141, compound

HRID 2395704Notes

Reaction equation

HRID 2395704 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]2[N:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:13][C:14]=2[CH3:15])=[N:6][CH:7]=1.Cl.N([O-])=O.[Na+].[I-:27].[Na+].C(=O)([O-])O.[Na+]>CC(C)=O.O>[I:27][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]2[N:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:13][C:14]=2[CH3:15])=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 10945878HCID 10945878, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18546141HCID 18546141, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent4×

Procedure

To a solution of 5-amino-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (7.10 g) in acetone (200 ml)-water (50 ml) was added dropwise concentrated hydrochloric acid (7.46 g) under ice cooling, and then solution of sodium nitrite (1.83 ) in water (10 ml) was added dropwise. The mixture was stirred for 10 minutes. To the mixture was added a solution of sodium iodide (4.40 g) in water (20 ml) under ice cooling. The mixture was stirred at 15°-20° C. for 2 hours. To the reaction mixture was added water, and the mixture was neutralized with a solution of sodium hydrogen carbonate. The mixture was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel chromatography. From the fraction eluted with ethyl acetate-hexane (1:9, v/v), crystals (6.65 g, 67%) of 5-iodo-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine were obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms. Melting point: 129°-130° C.

Workup

  1. stirringThe mixture was stirred at 15°-20° C. for 2 hours
  2. extractionThe mixture was subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-hexane (1:9, v/v)

Sources & evidence

ORD record
ord-9b1c0b5d5c834f2a96462fc4fede9f0b
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

Loading…