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

HRID 1267314

Reaction equation

HRID 1267314 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 5amino-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-f991b5d1cd8b47f4b1510e0211ced65c
Source dataset
uspto-grants-2003_04
Patent number
US06552058B1

Linked notes

Loading…