Sodium hydride → HCID 21833685, compound

HRID 1740816Notes

Reaction equation

HRID 1740816 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[N:10]1[N:11]([CH2:15][C:16]2[CH:25]=[CH:24][C:19]([O:20][CH2:21][CH2:22]Br)=[CH:18][CH:17]=2)[N:12]=[CH:13][CH:14]=1>CN(C)C=O>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[O:3][CH2:22][CH2:21][O:20][C:19]1[CH:24]=[CH:25][C:16]([CH2:15][N:11]2[N:12]=[CH:13][CH:14]=[N:10]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21833675HCID 21833675, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 21833685HCID 21833685, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a mixture of 5 ml of anhydrous N,N-dimethylformamide and 51 mg of sodium hydride (60% oil dispersion) is added dropwise an anhydrous N,N-dimethylformamide (3 ml) solution of 121 mg of 2-hydroxypyridine under stirring over 10 minutes. After stirring at room temperature for 1 hour, the mixture is cooled to 5° to 10° C., to which an anhydrous N,N-dimethylformamide (2 ml) solution of 300 mg of 2-[4-(2-2H-1,2,3-triazolyl)methylphenoxy]ethyl bromide is added dropwise over 30 minutes. The mixture is then stirred at room temperature overnight. The reaction mixture is poured into 50 ml of ice water, which is extracted with twice with 30 ml of toluene. The organic layers are combined, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography, which affords 4-(2-2H-1,2,3-triazolyl)methylphenyl 2-(2-pyridyloxy)ethyl ether.

Workup

  1. stirringAfter stirring at room temperature for 1 hour
  2. additionis added dropwise over 30 minutes
  3. stirringThe mixture is then stirred at room temperature overnight
  4. extractionis extracted with twice with 30 ml of toluene
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42067da0345345e39bc186934c408af5
Source dataset
uspto-grants-1999_10
Patent number
US05972949

Reaction notes

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