Sodium hydride → 1-[3-(3-benzyloxyphenyl)propyl]-1H-1,2,3-triazole

HRID 2084376Notes

Reaction equation

HRID 2084376 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].I[CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:16][CH:17]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([O:18][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][CH2:9][N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)[CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 22733348Benzyl 3-(3-iodopropyl)phenyl etherHCID 178418936HCID 178418936, compound

Product 1

HCID 121098701-[3-(3-benzyloxyphenyl)propyl]-1H-1,2,3-triazoleYield 37.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In an argon atmosphere, 1H-1,2,3-triazole (0.9 g) was dissolved in DMF (20 ml); 65% oily sodium hydride (0.48 g) was added. After stirring for 30 minutes, a solution of benzyl 3-(3-iodopropyl)phenyl ether (3.53 g) in DMF (5 ml) was added, followed by stirring at room temperature for 19 hours. The reaction mixture was diluted with ethyl acetate and washed with water and saturated saline. Under reduced pressure, the solvent was distilled off; the residue was subjected to column chromatography to yield the titled compound (1.1 g) as colorless crystals.

Workup

  1. stirringby stirring at room temperature for 19 hours
  2. washwashed with water and saturated saline
  3. distillationUnder reduced pressure, the solvent was distilled off

Sources & evidence

ORD record
ord-97cbaffd525341eaaf687188f14621fc
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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