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

HRID 2395699Notes

Reaction equation

HRID 2395699 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), a solution of sodium nitrite (NaNO2) (2.46 g) in water (10 ml) was added dropwise at a temperature of under 10° C. After mixture was stirred at 10° C. for 30 minutes, a solution of potassium iodide (KI) (2.46 g) in water (10 ml) was added dropwise to the mixture. The reaction mixture was stirred at 30° to 35° C. for 1 hour and then at 35° to 40° C. for 1 hour, after which it was concentrated under reduced pressure. The residue was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure. The residual oily substance was subjected to silica gel chromatography. From the fraction eluted with ethyl acetate-hexane (1:3, v/v), 5-iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (7.22 g, 52%) was obtained, which was then recrystallized from ethyl acetate-hexane to yield a colorless crystal.

Workup

  1. stirringThe reaction mixture was stirred at 30° to 35° C. for 1 hour
  2. waitat 35° to 40° C. for 1 hour
  3. concentrationafter which it was concentrated under reduced pressure
  4. additionThe residue was poured into water
  5. extractionextracted with ethyl acetate
  6. washAfter the ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationthe solvent was distilled off under reduced pressure
  9. washFrom the fraction eluted with ethyl acetate-hexane (1:3

Sources & evidence

ORD record
ord-b91a3c2a4f1a4082875a937a930ea69e
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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