Hydrochloric Acid → 5-Iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine

HRID 1857522Notes

Reaction equation

HRID 1857522 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[N:6][CH:7]=1.Cl.N([O-])=O.[Na+].[I-:28].[K+]>O.CC(C)=O>[I:28][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 110877225-Amino-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridineHCID 23668193Sodium Nitrite

Product 1

HCID 185461685-Iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridineYield 119.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

To a mixture of 5-amino-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (10.0 g), conc. HCl (8.47 ml) and acetone (100 ml) was added dropwise a solution of sodium nitrite (NaNO2) (2.46 g) in water (10 ml) at temperatures below 10° C. The mixture was stirred for 30 minutes at 10° C., to which was dropwise added a solution of potassium iodide (KI) (2.46 g) in water (10 ml) at 10° C. The reaction mixture was stirred for further one hour at temperatures raging from 30 to 35° C. and for another one hour at temperatures ranging from 35 to 40° C., followed by concentration under reduced pressure. The concentrate was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure. The residual oily product was subjected to a silica gel chromatography. From the fractions eluted with ethyl acetate-hexane (1:3, v/v) was obtained 5-iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (7.22 g, 52%). Recrystallization from ethyl acetate-hexane gave colorless crystals, m.p.105-106° C.

Workup

  1. stirringThe reaction mixture was stirred for further one hour at temperatures
  2. waitraging from 30 to 35° C. and for another one hour at temperatures
  3. customranging from 35 to 40° C.
  4. concentrationfollowed by concentration under reduced pressure
  5. additionThe concentrate was poured into water, which
  6. extractionwas subjected to extraction with ethyl acetate
  7. washThe ethyl acetate layer was washed with water
  8. dry with materialdried (MgSO4)
  9. distillationthe solvent was distilled off under reduced pressure
  10. washFrom the fractions eluted with ethyl acetate-hexane (1:3

Sources & evidence

ORD record
ord-1e2e3b8fa8b1439abf5bcfa9f0aeeed3
Source dataset
uspto-grants-2000_11
Patent number
US06147099

Reaction notes

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