Potassium Iodide → 1-[3-(4-nitro-phenoxy)-propyl]-1H-[1,2,3]triazole

HRID 1271412Notes

Reaction equation

HRID 1271412 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[NH:15]1[CH:19]=[CH:18][N:17]=[N:16]1.[I-].[K+].[OH-].[Na+]>CC(O)(CC)C>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:15]2[CH:19]=[CH:18][N:17]=[N:16]2)=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 118446171-(3-Chloropropoxy)-4-nitrobenzeneHCID 178418936HCID 178418936, compound

Product 1

HCID 184535181-[3-(4-nitro-phenoxy)-propyl]-1H-[1,2,3]triazole

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
120 °C

Procedure

1-(3-Chloro-propoxy)-4-nitro-benzene (7 g, 32.5 mmol) is dissolved in 2-methyl-2-butanol (35 ml) followed by the addition of 1H-1,2,3-triazole (3.43 g, 48.7 mmol), potassium iodide (0.54 g, 3.25 mmol) and sodium hydroxide (1.95 g, 48.7 mmol). The mixture is stirred for 20 h at 120° C., evaporated to dryness and suspended in toluene. Washing with water, drying over sodium sulfate and concentration in vacuo yields a crude product, which is washed with ether yielding 1-[3-(4-nitro-phenoxy)-propyl]-1H-[1,2,3]triazole as a colorless solid. Yield 6 g (75%)

Workup

  1. customevaporated to dryness
  2. washWashing with water
  3. dry with materialdrying over sodium sulfate and concentration in vacuo
  4. customyields a crude product, which
  5. washis washed with ether

Sources & evidence

ORD record
ord-f4d1b83b68d740f3ba350f72807f270d
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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